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Synthetic route

2-chloro-N-phenyl-3-oxobutanamide
31844-92-5

2-chloro-N-phenyl-3-oxobutanamide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With potassium carbonate; para-thiocresol In acetonitrile at 20℃; for 1h; Reagent/catalyst;100%
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 6 h / 20 °C
2: para-thiocresol; potassium carbonate / acetonitrile / 0.33 h / 20 °C
View Scheme
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In propan-1-ol at 30 - 50℃; for 5h; Solvent; Temperature; Autoclave; Large scale;98%
In cyclohexane at 25℃; Equilibrium constant; Rate constant;
With benzene
2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With sodium acetate In tetrahydrofuran for 24h; Reflux;98%
In water for 2.5h; Reflux; Green chemistry;94%
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;82%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
for 0.0833333h; Acylation; microwave irradiation;97%
for 0.1h; Microwave irradiation;94%
With silver trifluoromethanesulfonate In nitromethane at 80℃; for 8h;90%
3-(methylamino)-N-phenylbut-2-enamide
59846-49-0

3-(methylamino)-N-phenylbut-2-enamide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
Stage #1: 3-(methylamino)-N-phenylbut-2-enamide With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane Further stages.;
93%
3-phenylamino-2-[(phenylimino)methyl]acrylonitrile
154867-20-6

3-phenylamino-2-[(phenylimino)methyl]acrylonitrile

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

A

5-acetyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonitrile
1352630-34-2

5-acetyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carbonitrile

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In toluene at 110℃; for 0.166667h; Inert atmosphere;A 91%
B n/a
N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); oxygen In tetrahydrofuran at 25℃; for 16h; Reagent/catalyst; Sealed tube; Inert atmosphere;91%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In toluene at 25℃; for 48h;30%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry;88%
With natural kaolinitic clay In toluene Heating;60%
yttria-zirconia based Lewis acid catalyst In toluene for 3h; Acylation; Heating;59%
In toluene for 24h; Heating / reflux;50.3%
Heating;
allyl acetoacetate
1118-84-9

allyl acetoacetate

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 80℃; for 12h; Sealed tube; Green chemistry;87%
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In xylene Heating;83%
In toluene at 150℃; for 14h;56%
In toluene Reflux;
acetylketene
691-45-2

acetylketene

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
In benzene at 100℃;80%
2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

2-acetyl-4-phenyl-2H-1,4-thiazin-3(4H)-one

2-acetyl-4-phenyl-2H-1,4-thiazin-3(4H)-one

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 80℃; for 0.166667h;A 4%
B 70%
With hydrogenchloride In water; acetonitrile at 80℃; for 0.166667h; Product distribution; Mechanism; other 1,4-oxathiin-3-carboxamides, other reagent: H2SO4, other solvents: benzene, toluene, dioxane, THF, EtOH, various reagent concentration, various reaction temperature and time;A 4%
B 70%
With hydrogenchloride In water; acetonitrile at 80℃; for 0.166667h; other reagent: H2SO4;A 4%
B 70%
C10H10BrNO
1058721-69-9

C10H10BrNO

A

C10H9NO
1058721-80-4

C10H9NO

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In tetrahydrofuran for 12h; Inert atmosphere; Reflux;A 70%
B 25%
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In 1,4-dioxane for 3h; Inert atmosphere; Reflux;A 38%
B 40%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

A

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In toluene at 25℃; for 2h; Inert atmosphere;A 30%
B 70%
C10H10BrNO
1058721-69-9

C10H10BrNO

A

C10H9NO
1058721-80-4

C10H9NO

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C

Buta-2,3-dien-anilid
179242-29-6

Buta-2,3-dien-anilid

Conditions
ConditionsYield
With copper(l) iodide; 2-(2-methyl-1-oxopropyl)cyclohexanone; potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux;A 69%
B 6%
C 9%
With copper(l) iodide; potassium carbonate In tetrahydrofuran for 16h; Inert atmosphere; Reflux;A 17%
B 63%
C 16%
With copper(l) iodide; potassium carbonate; L-proline In tetrahydrofuran for 16h; Inert atmosphere; Reflux;A 25%
B 23%
C 30%
diazoacetone
2684-62-0

diazoacetone

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In toluene at 60℃; under 760.051 Torr; for 6h;67%
N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

trans-azoxybenzene
20972-43-4, 21650-65-7, 495-48-7

trans-azoxybenzene

Conditions
ConditionsYield
With water; copper dichloride In tetrahydrofuran at 30℃; for 48h; Inert atmosphere;A 18%
B 65%
di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

N-(buta-2,3-dien-1-yl)-N-phenylhydroxylamine

A

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

2-(tert-butoxy)-3-oxo-N-phenylbutanamide

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In toluene at 25℃; for 2h; Inert atmosphere;A 35%
B 65%
2-chloro-N-phenyl-3-oxobutanamide
31844-92-5

2-chloro-N-phenyl-3-oxobutanamide

para-thiocresol
106-45-6

para-thiocresol

A

C17H17NO2S

C17H17NO2S

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 0.666667h;A 56%
B 27%
With potassium carbonate In acetonitrile at 20℃; for 6h;A 40%
B 45%
carbon monoxide
201230-82-2

carbon monoxide

acetylacetone
123-54-6

acetylacetone

Phenyl azide
622-37-7

Phenyl azide

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With palladium dichloride In N,N-dimethyl acetamide at 70℃; for 12h; Schlenk technique;A 31%
B 53%
(Z)-3-(benzylamino)-N-phenylbut-2-enamide
59887-23-9

(Z)-3-(benzylamino)-N-phenylbut-2-enamide

A

3-oxo-2,5-dimethyl-1-benzyl-N2,N4-diphenyl-2,3-dihydro-1H-pyrrole-2,4-dicarboxylic acid amide
1002555-74-9

3-oxo-2,5-dimethyl-1-benzyl-N2,N4-diphenyl-2,3-dihydro-1H-pyrrole-2,4-dicarboxylic acid amide

B

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 4.5h;A 47%
B 21%
triethyl borane
97-94-9

triethyl borane

phenyl isocyanate
103-71-9

phenyl isocyanate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

A

1-ethyl-1-isopropyl-3-phenylurea

1-ethyl-1-isopropyl-3-phenylurea

B

2-(diisopropylamino)-N-phenylpropanamide

2-(diisopropylamino)-N-phenylpropanamide

C

N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

D

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With air at 20℃; for 14h; Further byproducts.;A 4%
B 43%
C 10%
D 23%
3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione
34132-56-4

3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione

ethanolamine
141-43-5

ethanolamine

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione
38756-99-9

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione

Conditions
ConditionsYield
With ethanol at 95 - 100℃; for 2h;A 15%
B 35%
crotonanilide
1733-40-0

crotonanilide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; palladium diacetate; acetic acid at 80℃; for 6h;34%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

aniline
62-53-3

aniline

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
for 0.0833333h; Microwave irradiation;A 30%
B 1.81 g
3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione
34132-56-4

3-phenyl-3,4-dihydro-6-methyl-2H-1,3-oxazine-2,4-dione

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione
38756-99-9

1-(2-hydroxyethyl)-6-methyl-3-phenyl-2,4(1H,3H)-pyrimidinedione

Conditions
ConditionsYield
With ethanolamine In N,N-dimethyl-formamide at 95 - 100℃; for 2h;A 28%
B 18%
ethanol
64-17-5

ethanol

diacetylacetanilide
18629-85-1

diacetylacetanilide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

ethanol
64-17-5

ethanol

3-methylamino-but-2-enoic acid anilide
49679-88-1

3-methylamino-but-2-enoic acid anilide

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

methylamine
74-89-5

methylamine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

aniline
62-53-3

aniline

A

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

B

ethyl 3-anilinocrotonate
6287-35-0

ethyl 3-anilinocrotonate

benzofurazan oxide
480-96-6

benzofurazan oxide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-N-Phenylcarbamyl-3-Methylquinoxaline-di-N-Oxide
31983-89-8

2-N-Phenylcarbamyl-3-Methylquinoxaline-di-N-Oxide

Conditions
ConditionsYield
Stage #1: benzofurazan oxide; N-phenylacetoacetamide In isopropyl alcohol at 60℃; for 0.5h;
Stage #2: With calcium hydroxide In isopropyl alcohol at 60℃;
100%
With 3 A molecular sieve In methanol for 24h; Ambient temperature;88%
In ethanol88%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

thiourea
17356-08-0

thiourea

1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide

1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 24h; Biginelli pyrimidine synthesis; Reflux;100%
With cobalt(II) nitrate hexahydrate In ethanol at 20℃; for 0.666667h;90%
With hydrogenchloride In ethanol for 3h; Heating;65%
With hydrogenchloride; aluminum (III) chloride In methanol; water Reflux;
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate

4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate

2,4,8-trimethyl-1,5,6,8a,9-pentaaza-fluorene-7-carboxylic acid phenylamide

2,4,8-trimethyl-1,5,6,8a,9-pentaaza-fluorene-7-carboxylic acid phenylamide

Conditions
ConditionsYield
With trimethylamine at 20℃; under 375.03 Torr; for 12h;100%
2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate

2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-[(4',6'-dimethyl-3'-cyano-2'-pyridinylthio)-2-phenylhydrazono]-3-oxo-N-phenylbutanamide

2-[(4',6'-dimethyl-3'-cyano-2'-pyridinylthio)-2-phenylhydrazono]-3-oxo-N-phenylbutanamide

Conditions
ConditionsYield
Stage #1: 2-(4,6-dimethyl-3-cyano-2-pyridinylthio)benzenediazonium nitrate; N-phenylacetoacetamide for 0.0833333h; grinding;
Stage #2: With trimethylamine at 20℃; under 375.038 Torr; for 12h; Further stages.;
100%
carbon disulfide
75-15-0

carbon disulfide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

dimethyl sulfate
77-78-1

dimethyl sulfate

2-[bis(methylsulfanyl)methylidene]-3-oxo-N-phenylbutanamide
145508-18-5

2-[bis(methylsulfanyl)methylidene]-3-oxo-N-phenylbutanamide

Conditions
ConditionsYield
Stage #1: N-phenylacetoacetamide With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide for 0.5h;
Stage #2: carbon disulfide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #3: dimethyl sulfate In N,N-dimethyl-formamide at 20℃; for 4.5h;
100%
Stage #1: N-phenylacetoacetamide With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: carbon disulfide In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #3: dimethyl sulfate In N,N-dimethyl-formamide at 20℃; for 4.5h;
96%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-methyl-2-(N-phenylcarbamoyl)methyl-1,2,3,4-tetrahydroquinazolin-4-one
81038-81-5

2-methyl-2-(N-phenylcarbamoyl)methyl-1,2,3,4-tetrahydroquinazolin-4-one

Conditions
ConditionsYield
With α-chymotrypsin In ethanol at 60℃; for 40h; Enzymatic reaction;99%
at 100℃; for 4h; under reduced pressure;55%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

(R)-3-hydroxy-N-phenylbutanamide
124095-27-8

(R)-3-hydroxy-N-phenylbutanamide

Conditions
ConditionsYield
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 60℃; under 22501.8 Torr; for 48h;99%
With hydrogen; {(RuCl[(R)-SYNPHOS])2(μ-Cl)3}[NH2Me2] In methanol at 50℃; under 7500.6 Torr; for 1h;92%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

1-acetylcyclopentanecarboxylic acid amide
951000-13-8

1-acetylcyclopentanecarboxylic acid amide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;94%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
4-acetyl-2-iodotrifluoroacetanilide

4-acetyl-2-iodotrifluoroacetanilide

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

5-acetyl-2-methyl-N-phenyl-1H-indole-3-carboxamide

5-acetyl-2-methyl-N-phenyl-1H-indole-3-carboxamide

Conditions
ConditionsYield
With water; caesium carbonate; L-proline; copper(l) iodide In dimethyl sulfoxide at 20℃;99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

ethylamine
75-04-7

ethylamine

3-ethylamino-but-2-enoic acid phenylamide

3-ethylamino-but-2-enoic acid phenylamide

Conditions
ConditionsYield
In dichloromethane; water for 5h;99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4-methyl-2-nitroaniline
89-62-3

4-methyl-2-nitroaniline

pigment yellow 1
2512-29-0

pigment yellow 1

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Time;99%
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.666667h; Green chemistry;99%
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride; C25H20N6O6S2; sodium nitrite In water at 10℃; for 1h;
Stage #2: N-phenylacetoacetamide With sodium acetate; acetic acid In water at 25 - 90℃; for 2.5h; pH=6;
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 10℃; for 1h;
Stage #2: N-phenylacetoacetamide With sodium hydroxide; sodium acetate; acetic acid In water at 25 - 90℃; for 2.5h; pH=6;
Stage #1: 4-methyl-2-nitroaniline With hydrogenchloride In water at 75 - 80℃; for 1h;
Stage #2: With sodium nitrite In water at 0 - 5℃; for 0.75h;
Stage #3: N-phenylacetoacetamide Further stages;
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2,2-difluoro-3-oxo-N-phenylbutanamide
1439365-74-8

2,2-difluoro-3-oxo-N-phenylbutanamide

Conditions
ConditionsYield
With 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2 2 2]octane bis(tetrafluoroborate); potassium carbonate In water at 20℃; for 5h;99%
With Selectfluor In water; acetonitrile at 20℃; for 16h; Schlenk technique; Sealed tube; chemoselective reaction;94%
C10H6BrClO2

C10H6BrClO2

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

1-{5-[(5-chloro-2-hydroxy-4-methylphenyl)carbonyl]-2-(phenylamino)furan-3-yl}ethan-1-one

1-{5-[(5-chloro-2-hydroxy-4-methylphenyl)carbonyl]-2-(phenylamino)furan-3-yl}ethan-1-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 20℃; regioselective reaction;99%
3,3'-dichlorobenzidine
91-94-1

3,3'-dichlorobenzidine

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C.I. pigment yellow 12

C.I. pigment yellow 12

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry;99%
Stage #1: 3,3'-dichlorobenzidine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Large scale;
Stage #2: N-phenylacetoacetamide With acetic acid; sodium hydroxide In water at 10 - 55℃; for 2.5h; pH=6.5 - 7; Reagent/catalyst; Large scale;
580 kg
2,6-di-tert-butyl-4-(2-hydroxy-5-methylbenzylidene)-2,5-cyclohexadiene-1-one

2,6-di-tert-butyl-4-(2-hydroxy-5-methylbenzylidene)-2,5-cyclohexadiene-1-one

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C32H37NO3

C32H37NO3

Conditions
ConditionsYield
Stage #1: 2,6-di-tert-butyl-4-(2-hydroxy-5-methylbenzylidene)cyclohexa-2,5-dienone; N-phenylacetoacetamide With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In dichloromethane at 20℃; for 48h;
Stage #2: With toluene-4-sulfonic acid In toluene at 110℃; for 1h; enantioselective reaction;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

pigment yellow 6
4106-76-7

pigment yellow 6

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water for 0.666667h;
Stage #2: N-phenylacetoacetamide In water at 20℃; for 0.166667h;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-nitro-aniline
88-74-4

2-nitro-aniline

pigment yellow 5
4106-67-6

pigment yellow 5

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: N-phenylacetoacetamide In water at 20℃; for 1h;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

4-nitro-aniline
100-01-6

4-nitro-aniline

pigment yellow 4
1657-16-5

pigment yellow 4

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.75h; Time; Reagent/catalyst;99%
With hydrogenchloride; sodium nitrite In water at 20℃; for 1.5h; Temperature; Green chemistry;99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

benzylamine
100-46-9

benzylamine

(Z)-3-(benzylamino)-N-phenylbut-2-enamide
59887-23-9

(Z)-3-(benzylamino)-N-phenylbut-2-enamide

Conditions
ConditionsYield
With tetrabutylammomium bromide In water at 20℃; for 12h;98%
With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃;68%
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-methyl-N-phenyl-1,8-naphthyridine-3-carboxamide
112697-61-7

2-methyl-N-phenyl-1,8-naphthyridine-3-carboxamide

Conditions
ConditionsYield
With lithium chloride for 0.0833333h; Friedlaender condensation; microwave irradiation;98%
With toluene-4-sulfonic acid at 20℃; for 5h; Friedlander condensation;92%
With zirconyl chloride octahydrate In neat (no solvent, solid phase) at 70 - 80℃; for 0.15h;92%
5,7-dimethylpyrazolo<4,3-c><1,2,5>oxadiazin-3(5H)-one
58663-95-9

5,7-dimethylpyrazolo<4,3-c><1,2,5>oxadiazin-3(5H)-one

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

1,3,6-Trimethyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid phenylamide
106538-03-8

1,3,6-Trimethyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid phenylamide

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 0.5h; Ambient temperature;98%
1,1-di(p-tolyl)ethylene
2919-20-2

1,1-di(p-tolyl)ethylene

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

6,6-bis(4-methylphenyl)-4-(phenylcarbamoyl)-3-methyl-1,2-dioxan-3-ol
139050-83-2, 139050-84-3

6,6-bis(4-methylphenyl)-4-(phenylcarbamoyl)-3-methyl-1,2-dioxan-3-ol

Conditions
ConditionsYield
With oxygen; manganese triacetate; acetic acid at 23℃; for 12h;98%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

Cysteamine
60-23-1

Cysteamine

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
122717-93-5

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 16h; Heating;98%
With toluene-4-sulfonic acid In benzene for 6h; Heating;98%
2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
122717-93-5

2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid; triethylamine In benzene for 6h; Heating;98%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

5-aminophenyl-3-methyl-1-phenyl-1H-pyrazole
22896-71-5

5-aminophenyl-3-methyl-1-phenyl-1H-pyrazole

Conditions
ConditionsYield
With pyridine; 2,4-{[3-[(CH2)5C8F17]-4-MeO-phenyl]}2-P2S2 2,4-disulfide In tetrahydrofuran at 55℃; for 14h;98%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

propargyl bromide
106-96-7

propargyl bromide

2-acetyl-N-phenyl-2-(prop-2-ynyl)pent-4-ynamide
1141891-26-0

2-acetyl-N-phenyl-2-(prop-2-ynyl)pent-4-ynamide

Conditions
ConditionsYield
Stage #1: N-phenylacetoacetamide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;
98%
With potassium carbonate In N,N-dimethyl-formamide; acetone; toluene at 20℃; for 16h;93%
In tetrahydrofuran at 20℃; for 9h;
2-[(trimethylsilyl)ethynyl]aniline
103529-16-4

2-[(trimethylsilyl)ethynyl]aniline

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

C18H16N2O
1220451-94-4

C18H16N2O

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 85℃; for 15h;98%

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