Product Name

  • Name

    Oxcarbazepine

  • EINECS 249-188-8
  • CAS No. 28721-07-5
  • Article Data37
  • CAS DataBase
  • Density 1.329 g/cm3
  • Solubility DMSO: ~9 mg/mL
  • Melting Point 215-216 °C
  • Formula C15H12N2O2
  • Boiling Point 457.2 °C at 760 mmHg
  • Molecular Weight 252.272
  • Flash Point 230.3 °C
  • Transport Information
  • Appearance Pale yellow powder
  • Safety 16-36/37
  • Risk Codes 22-36-20/21/22-11
  • Molecular Structure Molecular Structure of 28721-07-5 (Oxcarbazepine)
  • Hazard Symbols Xn,F
  • Synonyms Trileptal;GP 47680;5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-10-oxo-;Oxcarbazepine (USAN);Trileptal (TN);Oxcarbazepine [INN];Oxcarbazepina [INN-Spanish];10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carboxamide;Oxcarbazepinum [INN-Latin];
  • PSA 63.40000
  • LogP 3.40750

Synthetic route

10,11-dihydro-10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide
98253-74-8

10,11-dihydro-10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 1.3h; Solvent;95.7%
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

10,11-dihydro-5H-dibenzo[b,f]azepin-10-one
21737-58-6

10,11-dihydro-5H-dibenzo[b,f]azepin-10-one

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
In dichloromethane at 0 - 5℃; Inert atmosphere;93%
80%
Stage #1: isocyanate de chlorosulfonyle; 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one In dichloromethane at 25℃; for 17h;
Stage #2: With water Further stages.;		70%
Stage #1: isocyanate de chlorosulfonyle; 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one In chloroform at 20℃;
Stage #2: With water at 20℃;		56%
10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide
29331-92-8

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With peracetic acid; potassium dichromate; hydrogen In 1,2-dichloro-ethane at 20℃; for 1h;90%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dichloromethane at 25 - 30℃; for 0.25h;65.5%
Stage #1: 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dichloromethane at 25 - 30℃; for 0.25h;
Stage #2: With sodium hypochlorite; sodium hydrogencarbonate In dichloromethane; water at 0 - 5℃; for 1h; pH=9.7;		1.3 g
10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide
28721-09-7

10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 40℃; for 2h;88.5%
With hydrogenchloride In water at 25 - 85℃; for 4 - 6h;73%
With sulfuric acid at 25℃; for 17h;
methyl N-cyano-N-2'-cyanophenyl-2-aminophenylacetate

methyl N-cyano-N-2'-cyanophenyl-2-aminophenylacetate

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Stage #1: methyl N-cyano-N-2'-cyanophenyl-2-aminophenylacetate With potassium tert-butylate In tetrahydrofuran at 40 - 50℃; for 4h;
Stage #2: With water In tetrahydrofuran at 50 - 55℃; for 3h;		87.9%
ethyl N-cyano-N-2′-cyanophenyl-2-aminophenylacetate

ethyl N-cyano-N-2′-cyanophenyl-2-aminophenylacetate

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Stage #1: ethyl N-cyano-N-2′-cyanophenyl-2-aminophenylacetate With potassium tert-butylate In tetrahydrofuran at 40 - 50℃; for 4h;
Stage #2: With water In tetrahydrofuran at 60 - 65℃; for 3h;		86.4%
C16H13ClN2O4S

C16H13ClN2O4S

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With water; acetic acid at 15 - 25℃; for 0.5 - 1h;84%
10-chloro-5H-dibenzo[b,f]azepine-5-carboxamide
59690-92-5

10-chloro-5H-dibenzo[b,f]azepine-5-carboxamide

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 50h;83%
10-Brom-5-carbamoyl-5H-dibenzazepin
59690-97-0

10-Brom-5-carbamoyl-5H-dibenzazepin

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 50h;83%
10-methoxy-5H-dibenzo[b,f]azepine
4698-11-7

10-methoxy-5H-dibenzo[b,f]azepine

sodium isocyanate
917-61-3

sodium isocyanate

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With hydrogenchloride80%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With water; Pyridine hydrobromide In toluene at 22℃; for 7 - 8h;
Stage #2: With hydrogenchloride In water; toluene at 55 - 89℃; for 3 - 4h; Heating / reflux;		44%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With water; quinoline hydrochloride In toluene at 20℃; for 18h;
Stage #2: With hydrogenchloride In water; toluene at 89℃; for 2h; Heating / reflux;		35%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; sodium isocyanate With acetic acid at 25 - 35℃; for 1.33333 - 1.5h;
Stage #2: With sulfuric acid; water at 33 - 35℃; for 1 - 2h;
10-methoxy-5H-dibenzo[b,f]azepine
4698-11-7

10-methoxy-5H-dibenzo[b,f]azepine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In toluene at 10 - 15℃; for 6h;
Stage #2: With ammonia In water; toluene at 20℃; for 1h;
Stage #3: With formic acid; water for 1h; Product distribution / selectivity; Heating / reflux;		76.6%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With pyridine In toluene at 10 - 15℃; for 6h;
Stage #2: With ammonia In water; toluene at 20℃; for 1h;
Stage #3: With sulfuric acid; water for 1h; Product distribution / selectivity; Heating / reflux;		72.7%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In dichloromethane Heating / reflux;
Stage #2: With ammonia In dichloromethane; water at 20℃; for 1h;
Stage #3: With sulfuric acid; water for 1h; Product distribution / selectivity; Heating / reflux;		68.7%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 10 - 15℃; for 6h;
Stage #2: With ammonia In water; toluene at 20℃; for 1h;
Stage #3: With formic acid; water for 1h; Product distribution / selectivity; Heating / reflux;		67.3%
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine; bis(trichloromethyl) carbonate With triethylamine In toluene at 10 - 15℃; for 2 - 6h;
Stage #2: With ammonia In water; toluene at 20℃; for 1h;
Stage #3: With sulfuric acid; water for 1h; Product distribution / selectivity; Heating / reflux;		64%
10,11-Dihydrocarbamazepin
3564-73-6

10,11-Dihydrocarbamazepin

benzaldehyde
100-52-7

benzaldehyde

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With oxygen In acetic acid at 20℃; under 750.075 Torr; for 7 - 17h;49%
With oxygen In acetic acid at 22℃; for 7h;43%
With oxygen In acetonitrile at 20℃; under 750.075 Torr; for 17h;36%
10,11-Dihydrocarbamazepin
3564-73-6

10,11-Dihydrocarbamazepin

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; benzaldehyde; chromium(III) nitrate; nickel diacetate In acetic acid at 22℃; under 750.06 Torr; for 7h;26%
With oxygen at 20℃; under 750.075 Torr;16%
With sodium hypochlorite; tetrabutyl-ammonium chloride; ruthenium(III)chloride; copper dichloride In chloroform at 30 - 40℃; for 5h; Reagent/catalyst; Industrial scale;7.23 kg
10,11-Dihydrocarbamazepin
3564-73-6

10,11-Dihydrocarbamazepin

acetaldehyde
75-07-0

acetaldehyde

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With oxygen; N-hydroxyphthalimide In acetonitrile at 20℃; under 750.075 Torr; for 17h;19%
BIA 2-256
78880-64-5

BIA 2-256

A

platinum-on-carbon

platinum-on-carbon

B

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; palladium In waterA 5%
B n/a
10,11-Dihydrocarbamazepin
3564-73-6

10,11-Dihydrocarbamazepin

A

oxcarbazepine
28721-07-5

oxcarbazepine

B

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide
29331-92-8

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

C

10,11-dioxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

10,11-dioxo-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

D

10-hydroperoxy-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

10-hydroperoxy-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; benzaldehyde; nickel diacetate In acetic acid at 22℃; under 750.06 Torr; for 5h; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; reaction time;A 27 % Chromat.
B 9 % Chromat.
C 1 % Chromat.
D 10 % Chromat.
...Expand
carbamazepine 10,11-epoxide
36507-30-9

carbamazepine 10,11-epoxide

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With lithium iodide In chloroform
Multi-step reaction with 2 steps
1: triethylamine; 5%-palladium/activated carbon; hydrogen / water; methanol / 2 h / 750.08 Torr
2: peracetic acid; hydrogen; potassium dichromate / 1,2-dichloro-ethane / 1 h / 20 °C
View Scheme
10-methoxy-5H-dibenz[b,f]azepine-5-carbonitrile

10-methoxy-5H-dibenz[b,f]azepine-5-carbonitrile

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 20℃; for 0.0833333 - 0.166667h;
1-(2-aminophenyl)-2-(2-bromophenyll)ethanone
869668-73-5

1-(2-aminophenyl)-2-(2-bromophenyll)ethanone

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 91 percent / Pd(OAc)2; BINAP; K3PO4 / toluene; H2O / 5 h / 130 °C
2.1: CHCl3 / 20 °C
2.2: 56 percent / H2O / 20 °C
View Scheme
2-(2-bromophenyl)-1-[2-N-(4-methylbenzenesulfonamido)phenyl]ethanone
869668-71-3

2-(2-bromophenyl)-1-[2-N-(4-methylbenzenesulfonamido)phenyl]ethanone

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 95 percent / H2SO4 / 0.17 h / 20 °C
2.1: 91 percent / Pd(OAc)2; BINAP; K3PO4 / toluene; H2O / 5 h / 130 °C
3.1: CHCl3 / 20 °C
3.2: 56 percent / H2O / 20 °C
View Scheme
N-(2-acetylphenyl)-4-methylbenzenesulfonamide
1859-70-7

N-(2-acetylphenyl)-4-methylbenzenesulfonamide

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 86 percent / Pd(OAc)2; Xantphos; Cs2CO3 / toluene; H2O / 48 h / 120 °C
2.1: 95 percent / H2SO4 / 0.17 h / 20 °C
3.1: 91 percent / Pd(OAc)2; BINAP; K3PO4 / toluene; H2O / 5 h / 130 °C
4.1: CHCl3 / 20 °C
4.2: 56 percent / H2O / 20 °C
View Scheme
2-aminoacetophenone
551-93-9

2-aminoacetophenone

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 96 percent / pyridine / CH2Cl2
2.1: 86 percent / Pd(OAc)2; Xantphos; Cs2CO3 / toluene; H2O / 48 h / 120 °C
3.1: 95 percent / H2SO4 / 0.17 h / 20 °C
4.1: 91 percent / Pd(OAc)2; BINAP; K3PO4 / toluene; H2O / 5 h / 130 °C
5.1: CHCl3 / 20 °C
5.2: 56 percent / H2O / 20 °C
View Scheme
1-phenyl-1,3-dihydro-indol-2-one
3335-98-6

1-phenyl-1,3-dihydro-indol-2-one

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 97 percent / aq. NaOH / 6 h / 100 °C
2.1: 98 percent / dimethylformamide / 4 h / 24 °C
3.1: 98 percent / Et3N; DMAP / CH2Cl2 / 3.5 h / 20 - 40 °C
4.1: 95 percent / hydrogen / Pd/C / methanol / 3 h / 30 °C
5.1: 40 percent / polyphosphoric acid / toluene / 11 h / 110 °C
6.1: aq. Na2CO3 / methanol; H2O / 0.5 h / 23 °C
7.1: CH2Cl2 / 17 h / 25 °C
7.2: 70 percent / H2O
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide / tetrahydrofuran / 5 h / 67 °C
1.2: 2 h / -10 °C
2.1: polyphosphoric acid / 3 h / 90 - 95 °C
3.1: water / 0 - 98 °C
4.1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
5.1: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
6.1: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide / tetrahydrofuran / 5 h / 67 °C
1.2: 2 h / -40 °C
2.1: polyphosphoric acid / 3 h / 90 - 95 °C
3.1: water / 0 - 98 °C
4.1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
5.1: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
6.1: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
Multi-step reaction with 9 steps
1.1: sodium hydroxide / water; ethanol / 1 h / 50 °C
1.2: 4 h / 20 °C
2.1: pyridine / toluene / 24 h / 50 °C
3.1: pyridine / 22 h / 100 °C
4.1: sodium hydroxide / water; methanol / 24 h / 20 °C
5.1: polyphosphoric acid / 3 h / 90 - 95 °C
6.1: water / 0 - 98 °C
7.1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
8.1: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
10-methoxy-5H-dibenzo[b,f]azepine
4698-11-7

10-methoxy-5H-dibenzo[b,f]azepine

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AcOH / 7 h / 25 °C
2: H2SO4 / 17 h / 25 °C
View Scheme
With hydrogenchloride; benzoic acid In water; toluene
With sulfuric acid In water; toluene
Multi-step reaction with 2 steps
1: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
2: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
(2-phenylamino-phenyl)-acetic acid methyl ester
39507-06-7

(2-phenylamino-phenyl)-acetic acid methyl ester

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: pyridine / toluene / 24 h / 50 °C
1.2: pyridine / 22 h / 100 °C
2.1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C
3.1: polyphosphoric acid / 3 h / 95 °C
4.1: 97 percent / aq. NaOH / 6 h / 100 °C
5.1: 98 percent / dimethylformamide / 4 h / 24 °C
6.1: 98 percent / Et3N; DMAP / CH2Cl2 / 3.5 h / 20 - 40 °C
7.1: 95 percent / hydrogen / Pd/C / methanol / 3 h / 30 °C
8.1: 40 percent / polyphosphoric acid / toluene / 11 h / 110 °C
9.1: aq. Na2CO3 / methanol; H2O / 0.5 h / 23 °C
10.1: CH2Cl2 / 17 h / 25 °C
10.2: 70 percent / H2O
View Scheme
Multi-step reaction with 7 steps
1.1: pyridine / toluene / 24 h / 50 °C
1.2: pyridine / 22 h / 100 °C
2.1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C
3.1: 70 percent / polyphosphoric acid / 3 h / 95 °C
4.1: 81 percent / p-TsOH / methanol / 5 h / Heating
5.1: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C
6.1: AcOH / 7 h / 25 °C
7.1: H2SO4 / 17 h / 25 °C
View Scheme
Multi-step reaction with 5 steps
1.1: pyridine / toluene / 24 h / 50 °C
1.2: pyridine / 22 h / 100 °C
2.1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C
3.1: 70 percent / polyphosphoric acid / 3 h / 95 °C
4.1: 72 percent / KOH / ethane-1,2-diol / 0.5 h / 108 °C
5.1: CH2Cl2 / 17 h / 25 °C
5.2: 70 percent / H2O
View Scheme
Multi-step reaction with 8 steps
1: pyridine / toluene / 24 h / 50 °C
2: pyridine / 22 h / 100 °C
3: sodium hydroxide / water; methanol / 24 h / 20 °C
4: polyphosphoric acid / 3 h / 90 - 95 °C
5: water / 0 - 98 °C
6: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
7: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
8: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester
353497-31-1

10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / p-TsOH / methanol / 5 h / Heating
2: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C
3: AcOH / 7 h / 25 °C
4: H2SO4 / 17 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 72 percent / KOH / ethane-1,2-diol / 0.5 h / 108 °C
2.1: CH2Cl2 / 17 h / 25 °C
2.2: 70 percent / H2O
View Scheme
Multi-step reaction with 4 steps
1: water / 0 - 98 °C
2: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
3: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
4: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
[2-(methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid methyl ester
805236-74-2

[2-(methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid methyl ester

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C
2.1: polyphosphoric acid / 3 h / 95 °C
3.1: 97 percent / aq. NaOH / 6 h / 100 °C
4.1: 98 percent / dimethylformamide / 4 h / 24 °C
5.1: 98 percent / Et3N; DMAP / CH2Cl2 / 3.5 h / 20 - 40 °C
6.1: 95 percent / hydrogen / Pd/C / methanol / 3 h / 30 °C
7.1: 40 percent / polyphosphoric acid / toluene / 11 h / 110 °C
8.1: aq. Na2CO3 / methanol; H2O / 0.5 h / 23 °C
9.1: CH2Cl2 / 17 h / 25 °C
9.2: 70 percent / H2O
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C
2: 70 percent / polyphosphoric acid / 3 h / 95 °C
3: 81 percent / p-TsOH / methanol / 5 h / Heating
4: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C
5: AcOH / 7 h / 25 °C
6: H2SO4 / 17 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 90 percent / aq. NaOH / methanol / 24 h / 25 °C
2.1: 70 percent / polyphosphoric acid / 3 h / 95 °C
3.1: 72 percent / KOH / ethane-1,2-diol / 0.5 h / 108 °C
4.1: CH2Cl2 / 17 h / 25 °C
4.2: 70 percent / H2O
View Scheme
Multi-step reaction with 6 steps
1: sodium hydroxide / water; methanol / 24 h / 20 °C
2: polyphosphoric acid / 3 h / 90 - 95 °C
3: water / 0 - 98 °C
4: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
5: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
6: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
10-methoxy-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester
353497-37-7

10-methoxy-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C
2: AcOH / 7 h / 25 °C
3: H2SO4 / 17 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
2: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
3: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
2-[(methoxycarbonyl)phenylamino]benzeneacetic acid
353497-35-5

2-[(methoxycarbonyl)phenylamino]benzeneacetic acid

oxcarbazepine
28721-07-5

oxcarbazepine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: polyphosphoric acid / 3 h / 95 °C
2.1: 97 percent / aq. NaOH / 6 h / 100 °C
3.1: 98 percent / dimethylformamide / 4 h / 24 °C
4.1: 98 percent / Et3N; DMAP / CH2Cl2 / 3.5 h / 20 - 40 °C
5.1: 95 percent / hydrogen / Pd/C / methanol / 3 h / 30 °C
6.1: 40 percent / polyphosphoric acid / toluene / 11 h / 110 °C
7.1: aq. Na2CO3 / methanol; H2O / 0.5 h / 23 °C
8.1: CH2Cl2 / 17 h / 25 °C
8.2: 70 percent / H2O
View Scheme
Multi-step reaction with 5 steps
1: 70 percent / polyphosphoric acid / 3 h / 95 °C
2: 81 percent / p-TsOH / methanol / 5 h / Heating
3: 98 percent / aq. NaOH / various solvent(s) / 4 h / 100 °C
4: AcOH / 7 h / 25 °C
5: H2SO4 / 17 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 70 percent / polyphosphoric acid / 3 h / 95 °C
2.1: 72 percent / KOH / ethane-1,2-diol / 0.5 h / 108 °C
3.1: CH2Cl2 / 17 h / 25 °C
3.2: 70 percent / H2O
View Scheme
Multi-step reaction with 5 steps
1: polyphosphoric acid / 3 h / 90 - 95 °C
2: water / 0 - 98 °C
3: sodium hydroxide / water; methanol / 2.5 h / 105 - 110 °C
4: acetic acid / 6.17 h / 20 - 45 °C / Inert atmosphere
5: hydrogenchloride / water; acetone / 2 h / 40 °C
View Scheme
oxcarbazepine
28721-07-5

oxcarbazepine

S-licarbazepine
104746-04-5

S-licarbazepine

Conditions
ConditionsYield
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;99%
Stage #1: oxcarbazepine With triethylammonium formate; C33H40ClN2O4RuS In ethyl acetate; N,N-dimethyl-formamide pH=6.8 - 7.45; Heating / reflux;
Stage #2: With formic acid In water; ethyl acetate; N,N-dimethyl-formamide for 23h; pH=7.4 - 7.8; Heating / reflux;		94%
Stage #1: oxcarbazepine With triethylamine; C33H40ClN2O4RuS In water; ethyl acetate; N,N-dimethyl-formamide at 72 - 77℃; pH=8.8; Heating / reflux;
Stage #2: With formic acid In water; ethyl acetate; N,N-dimethyl-formamide for 20 - 27h; pH=7.4; Heating / reflux;		88%
oxcarbazepine
28721-07-5

oxcarbazepine

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide
29331-92-8

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water at 20 - 45℃; for 1.5h;97.3%
With sodium tetrahydroborate In ethanol; water at 45 - 50℃;94%
With sodium tetrahydroborate; water In methanol at 25 - 65℃; for 2.75h;93.8%
oxcarbazepine
28721-07-5

oxcarbazepine

carbamazepin
298-46-4

carbamazepin

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 45 - 50℃; for 3h;91.5%
oxcarbazepine
28721-07-5

oxcarbazepine

5H-dibenzazepine-10(11H),11-dione
19579-83-0

5H-dibenzazepine-10(11H),11-dione

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane for 7h; Reflux;90%
With dihydrogen peroxide; methyltrioxorhenium(VII) In water; tert-butyl alcohol at 40℃; for 16h;27%
Multi-step reaction with 2 steps
1: 73.4 percent / Br2 / acetic acid / 60 h / 15 °C
2: 2.4 percent / acetic acid / 0.75 h / Heating
View Scheme
oxcarbazepine
28721-07-5

oxcarbazepine

acetic anhydride
108-24-7

acetic anhydride

10-acetoxy-5H-dibenzo[b,f]azepine-5-carboxamide
952740-00-0

10-acetoxy-5H-dibenzo[b,f]azepine-5-carboxamide

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 4.16h;88%
oxcarbazepine
28721-07-5

oxcarbazepine

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

10-methoxyimino-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

10-methoxyimino-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

Conditions
ConditionsYield
With pyridine In ethanol for 4h; Heating;87%
oxcarbazepine
28721-07-5

oxcarbazepine

A

(Z)-10,11-dihydro-10-hydroxyimino-5H-dibenzo[b,f]azepine-5-carboxamide

(Z)-10,11-dihydro-10-hydroxyimino-5H-dibenzo[b,f]azepine-5-carboxamide

B

10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide
461670-31-5

10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5-carboxamide

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol for 4h; Heating; Title compound not separated from byproducts;A n/a
B 86%
oxcarbazepine
28721-07-5

oxcarbazepine

methylthiol
74-93-1

methylthiol

10-Methylthio-5H-dibenzoazepin-5-carboxamid
92483-89-1

10-Methylthio-5H-dibenzoazepin-5-carboxamid

Conditions
ConditionsYield
With aluminium trichloride In chloroform for 5h; Heating;85%
oxcarbazepine
28721-07-5

oxcarbazepine

10-bromo-10,11-dihydro-11-oxo-5H-dibenzazepine-5-carboxamide

10-bromo-10,11-dihydro-11-oxo-5H-dibenzazepine-5-carboxamide

Conditions
ConditionsYield
With bromine In acetic acid at 15℃; for 60h;73.4%
oxcarbazepine
28721-07-5

oxcarbazepine

phenylhydrazine
100-63-0

phenylhydrazine

10-phenylhydrazono-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide

10-phenylhydrazono-10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate In ethanol; water at 60℃; for 0.5h;72.5%
oxcarbazepine
28721-07-5

oxcarbazepine

acetic acid
64-19-7

acetic acid

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

10-(2-Acetoxyethylthio)-5H-dibenzoazepin-5-carboxamid

10-(2-Acetoxyethylthio)-5H-dibenzoazepin-5-carboxamid

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 48h; Ambient temperature;72%
...Expand
oxcarbazepine
28721-07-5

oxcarbazepine

methyl glyoxylate methyl hemi-acetal
109745-70-2, 19757-97-2

methyl glyoxylate methyl hemi-acetal

Hydroxy-[(10-oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl)-amino]-acetic acid methyl ester

Hydroxy-[(10-oxo-10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl)-amino]-acetic acid methyl ester

Conditions
ConditionsYield
In chloroform for 2h; Heating;70%
oxcarbazepine
28721-07-5

oxcarbazepine

hydrazine carboxamide
4426-72-6, 51433-48-8

hydrazine carboxamide

C16H15N5O2

C16H15N5O2

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate In ethanol; water at 60℃; for 0.5h;68%
oxcarbazepine
28721-07-5

oxcarbazepine

thiosemicarbazide
79-19-6

thiosemicarbazide

C16H15N5OS

C16H15N5OS

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate In ethanol; water at 60℃; for 0.5h;61%
oxcarbazepine
28721-07-5

oxcarbazepine

10,11-dihydro-5H-dibenzo[b,f]azepin-10-one
21737-58-6

10,11-dihydro-5H-dibenzo[b,f]azepin-10-one

Conditions
ConditionsYield
With hydrogenchloride; 1-amino-3-(dimethylamino)propane In water; dimethyl sulfoxide at 120℃; for 1h;59%
With water
oxcarbazepine
28721-07-5

oxcarbazepine

1-butanethiol
109-79-5

1-butanethiol

10-Butylsulfanyl-dibenzo[b,f]azepine-5-carboxylic acid amide

10-Butylsulfanyl-dibenzo[b,f]azepine-5-carboxylic acid amide

Conditions
ConditionsYield
With aluminium trichloride In chloroform at 40℃; for 5h;58%
oxcarbazepine
28721-07-5

oxcarbazepine

O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

10-benzyloxyimino-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

10-benzyloxyimino-10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid amide

Conditions
ConditionsYield
With pyridine In ethanol for 4h; Heating;58%
oxcarbazepine
28721-07-5

oxcarbazepine

ethanethiol
75-08-1

ethanethiol

10-Ethylsulfanyl-dibenzo[b,f]azepine-5-carboxylic acid amide

10-Ethylsulfanyl-dibenzo[b,f]azepine-5-carboxylic acid amide

Conditions
ConditionsYield
With aluminium trichloride In chloroform at 40℃; for 5h;55.2%
oxcarbazepine
28721-07-5

oxcarbazepine

methylamine
74-89-5

methylamine

10-(methylamino)-5H-dibenzo[b,f]azepine-5-carboxamide
1548175-75-2

10-(methylamino)-5H-dibenzo[b,f]azepine-5-carboxamide

Conditions
ConditionsYield
Stage #1: oxcarbazepine; methylamine With titanium(IV) isopropylate In ethanol for 6h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In ethanol for 3h; Inert atmosphere;		52%

Oxcarbazepine History

In 1966,Oxcarbazepine(28721-07-5): was first synthesized, and it wasapproved for use as an anticonvulsant in Denmark in 1990. It was approved in Spain in 1993, in Portugal in 1997, and eventually for all other EU countries in 1999. It was approved in the US in 2000.

Oxcarbazepine Specification

1. Introduction of Oxcarbazepine
Oxcarbazepine is one kind of yellow to pale yellow crystalline powder. The IUPAC name of this chemical is 5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide. With the CAS registry number 28721-07-5, it is also named as 10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepin-5-carboxamid. The product's categories are Heterocyclic Compounds; APIs; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, the Classification Code of this chemical is Anticonvulsant; Anticonvulsants; Antiepileptic; Central Nervous System Agents; Reproductive Effect. Oxcarbazepine is a poorly water-soluble.

2. Properties of Oxcarbazepine
Physical properties about Oxcarbazepine are:
(1)ACD/LogP: 1.44; (2)ACD/LogD (pH 5.5): 1.44; (3)ACD/LogD (pH 7.4): 1.44; (4)ACD/BCF (pH 5.5): 7.27; (5)ACD/BCF (pH 7.4): 7.27; (6)ACD/KOC (pH 5.5): 143.92; (7)ACD/KOC (pH 7.4): 143.92; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)Polar Surface Area: 40.62 Å2; (11)Index of Refraction: 1.661; (12)Molar Refractivity: 70.21 cm3; (13)Molar Volume: 189.7 cm3; (14)Polarizability: 27.83×10-24cm3; (15)Surface Tension: 61.2 dyne/cm; (16)Density: 1.329 g/cm3; (17)Flash Point: 230.3 °C; (18)Enthalpy of Vaporization: 71.73 kJ/mol; (19)Boiling Point: 457.2 °C at 760 mmHg; (20)Vapour Pressure: 1.52E-08 mmHg at 25°C.

3. Structure Descriptors of Oxcarbazepine
You can still convert the following datas into molecular structure:
(1)SMILES: O=C3c1c(cccc1)N(c2ccccc2C3)C(=O)N
(2)InChI: InChI=1/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
(3)InChIKey: CTRLABGOLIVAIY-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
(5)Std. InChIKey: CTRLABGOLIVAIY-UHFFFAOYSA-N

4. Physical Properties of Oxcarbazepine

Physical Property Value Units Temp (deg C) Source
Melting Point 215.5 deg C   EXP
log P (octanol-water) 1.110 (none)   EST
Atmospheric OH Rate Constant 2.81E-11 cm3/molecule-sec 25 EST

5. Production of Oxcarbazepine
Preparation: this chemical can be prepared by 10 - methoxy-5H-dibenzo [b, f] aza and phosgene in toluene environment. Reaction is as follows:



6. Safety Information of Oxcarbazepine
WGK Germany: 3
RTECS: HN8445000

7. Uses of Oxcarbazepine
The Oxcarbazepine is an organic compound with the formula C15H12N2O2. Besides, it is a pale yellow powder, which is an anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy and bipolar disorder, and also used to treat anxiety disorders. Besides, it is a metabolite of Eslicarbazepine acetate, (BIA 2-093), a novel central nervous system drug.

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