Product Name

  • Name

    1-Methyl-5-amino-1H-benzimidazole-2-butanoic acid ethyl ester

  • EINECS 680-673-0
  • CAS No. 3543-73-5
  • Article Data7
  • CAS DataBase
  • Density 1.21 g/cm3
  • Solubility
  • Melting Point 130-135 °C
  • Formula C14H19N3O2
  • Boiling Point 471.6 °C at 760 mmHg
  • Molecular Weight 261.324
  • Flash Point 239 °C
  • Transport Information
  • Appearance Brown solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 3543-73-5 (1-Methyl-5-amino-1H-benzimidazole-2-butanoic acid ethyl ester)
  • Hazard Symbols
  • Synonyms 2-Benzimidazolebutyricacid, 5-amino-1-methyl-, ethyl ester (7CI,8CI);
  • PSA 70.14000
  • LogP 2.62250

Synthetic route

4‐(1‐methyl‐5‐nitro‐1H‐benzoimidazol‐2‐yl)butyric acid ethyl ester
3543-72-4

4‐(1‐methyl‐5‐nitro‐1H‐benzoimidazol‐2‐yl)butyric acid ethyl ester

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate at 20℃; for 16h;98.3%
With 5% Pd/C-iron; hydrogen In ethanol under 3000.3 Torr;87.5%
With 5%-palladium/activated carbon; hydrogen In methanol; acetic acid at 25℃; under 750.075 - 1500.15 Torr; for 15h;77.8%
6-fluoro-3-nitroaniline
369-36-8

6-fluoro-3-nitroaniline

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / toluene / 4 h / 85 °C
1.2: 3 h / 75 °C
2.1: sulfuric acid / 10 h / Reflux
3.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / 70 - 85 °C
2.1: water / 3 h / 75 °C
2.2: 55 - 60 °C
3.1: sulfuric acid / 10 h / Reflux
4.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr
View Scheme
glutaric anhydride,
108-55-4

glutaric anhydride,

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / toluene / 4 h / 85 °C
1.2: 3 h / 75 °C
2.1: sulfuric acid / 10 h / Reflux
3.1: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / 70 - 85 °C
2.1: water / 3 h / 75 °C
2.2: 55 - 60 °C
3.1: sulfuric acid / 10 h / Reflux
4.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr
View Scheme
4-(1-methyl-5-nitro-1H-benzimidazol-2-yl)butanoic acid
31349-48-1

4-(1-methyl-5-nitro-1H-benzimidazol-2-yl)butanoic acid

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 10 h / Reflux
2: 5% Pd/C-iron; hydrogen / ethanol / 3000.3 Torr
View Scheme
5-(2-fluoro-5-nitroanilino)-5-oxopentanoic acid
451459-95-3

5-(2-fluoro-5-nitroanilino)-5-oxopentanoic acid

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water / 3 h / 75 °C
1.2: 55 - 60 °C
2.1: sulfuric acid / 10 h / Reflux
3.1: ferrous(II) sulfate heptahydrate; hydrogen; Iron(III) nitrate nonahydrate; 5% Pd/C / ethanol / 3000.3 Torr
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoic‐2,2,4,4‐d4 acid hydrochloride

4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoic‐2,2,4,4‐d4 acid hydrochloride

Conditions
ConditionsYield
With water; water-d2; hydrogen chloride at 180℃; for 1.5h; Microwave irradiation; Sealed tube;93.5%
2,4-dinitrobenzoyl chloride
20195-22-6

2,4-dinitrobenzoyl chloride

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

ethyl 4-(5-(2,4-dinitrobenzamido)-1-methyl-1H-benzimidazol-2-yl)butanoate
1227860-30-1

ethyl 4-(5-(2,4-dinitrobenzamido)-1-methyl-1H-benzimidazol-2-yl)butanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;83%
benzyl bromide
100-39-0

benzyl bromide

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

ethyl 4-(5-(dibenzylamino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate

ethyl 4-(5-(dibenzylamino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 24h;82.9%
oxirane
75-21-8

oxirane

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester
3543-74-6

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester

Conditions
ConditionsYield
Stage #1: oxirane; ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate With sodium acetate trihydrate In water; acetic acid at 0 - 25℃; for 23h;
Stage #2: With potassium carbonate In dichloromethane at 20 - 25℃;		78.53%
With acetic acid In water at -5 - 0℃;78.5%
Stage #1: ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate With acetic acid In water at 0 - 5℃;
Stage #2: oxirane In water at 0 - 20℃; for 1.5h;
oxirene
157-18-6

oxirene

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester
3543-74-6

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester

Conditions
ConditionsYield
With sodium acetate; acetic acid In water at 0 - 25℃; for 23h; Concentration; Temperature; Time; Reagent/catalyst; Solvent;78.53%
2-(2-bromoethoxy)ethan-1-ol
57641-66-4

2-(2-bromoethoxy)ethan-1-ol

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

C18H27N3O4

C18H27N3O4

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 85℃;66%
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

2-bromoethanol
540-51-2

2-bromoethanol

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester
3543-74-6

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester

Conditions
ConditionsYield
With calcium carbonate In acetonitrile at 80 - 90℃;56.3%
With potassium carbonate In water at 69 - 70℃; for 13.5h; pH=4.2 - 5.5; Large scale;343.5 g
With diammonium phosphate; potassium iodide In water at 65 - 70℃; pH=4.2 - 5.5; Reagent/catalyst; pH-value; Temperature;17.2 g
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

2-chloro-ethanol
107-07-3

2-chloro-ethanol

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester
3543-74-6

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester

Conditions
ConditionsYield
With sodium carbonate; sodium iodide at 20 - 70℃;
With sodium carbonate; sodium iodide at 65 - 70℃;10 g
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

lithium 4-[1-methyl-5-bis-(2-chloroethyl)-benzimidazolyl-2] butanoate

lithium 4-[1-methyl-5-bis-(2-chloroethyl)-benzimidazolyl-2] butanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate; acetic acid / water / 23 h / 0 - 25 °C
2: thionyl chloride / dichloromethane / 6 h / Reflux
3: lithium hydroxide / water; acetone / 6 h / 15 - 20 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4-{5-[bis(2-chloro-ethyl)amino]-1-methyl-2-benzimidazolyl}butyric acid hydrochloride

4-{5-[bis(2-chloro-ethyl)amino]-1-methyl-2-benzimidazolyl}butyric acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium acetate; acetic acid / water / 23 h / 0 - 25 °C
2: thionyl chloride / dichloromethane / 6 h / Reflux
3: lithium hydroxide / water; acetone / 6 h / 15 - 20 °C
4: hydrogenchloride / water / 65 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium acetate trihydrate / water; acetic acid / 23 h / 0 - 25 °C
1.2: 20 - 25 °C
2.1: thionyl chloride / dichloromethane / 6 h / 35 - 45 °C
3.1: lithium hydroxide monohydrate / water; acetone / 15 - 20 °C
4.1: hydrogenchloride / water / 65 °C
View Scheme
Multi-step reaction with 4 steps
1: calcium carbonate / acetonitrile / 80 - 90 °C
2: thionyl chloride / dichloromethane / 6 h / 35 - 45 °C
3: lithium hydroxide monohydrate / water; acetone / 15 - 20 °C
4: hydrogenchloride / water / 65 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester

4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium acetate; acetic acid / water / 23 h / 0 - 25 °C
2: thionyl chloride / dichloromethane / 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: calcium carbonate / acetonitrile / 80 - 90 °C
2: thionyl chloride / dichloromethane / 6 h / 35 - 45 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid / water / -5 - 0 °C
2: thionyl chloride / dichloromethane / 2 h / -5 - 20 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

bendamustine hydrochloride
3543-75-7

bendamustine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium carbonate; sodium iodide / 65 - 70 °C
2.1: thionyl chloride / dichloromethane / 0 °C / Reflux
2.2: 80 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale
2: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
3: hydrogenchloride / water; acetone / 40 - 75 °C
View Scheme
Multi-step reaction with 3 steps
1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5
2: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
3: hydrogenchloride / water; acetone / 40 - 75 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5
2.1: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
2.2: 75 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / water / -5 - 0 °C
2: thionyl chloride / dichloromethane / 2 h / -5 - 20 °C
3: hydrogenchloride / water / 4 h / Reflux
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

bendamustine
16506-27-7

bendamustine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium iodide; diammonium phosphate / water / 65 - 70 °C / pH 4.2 - 5.5
2: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

bendamustine hydrochloride

bendamustine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / Large scale
2: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
View Scheme
Multi-step reaction with 2 steps
1: diammonium hydrogenphosphate / water / 65 - 70 °C / pH 4.2 - 5.5
2: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

2-bromoethanol
540-51-2

2-bromoethanol

A

C20H32N3O5(1+)*Br(1-)

C20H32N3O5(1+)*Br(1-)

B

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester
3543-74-6

4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester

Conditions
ConditionsYield
With diammonium hydrogenphosphate In water at 65 - 70℃; pH=4.2 - 5.5;
...Expand
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

lithium 4-[1-methyl-5-bis-(2-chloroethyl)-benzimidazolyl-2]butanoate

lithium 4-[1-methyl-5-bis-(2-chloroethyl)-benzimidazolyl-2]butanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium acetate trihydrate / water; acetic acid / 23 h / 0 - 25 °C
1.2: 20 - 25 °C
2.1: thionyl chloride / dichloromethane / 6 h / 35 - 45 °C
3.1: lithium hydroxide monohydrate / water; acetone / 15 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: calcium carbonate / acetonitrile / 80 - 90 °C
2: thionyl chloride / dichloromethane / 6 h / 35 - 45 °C
3: lithium hydroxide monohydrate / water; acetone / 15 - 20 °C
View Scheme
chloroacetic acid
79-11-8

chloroacetic acid

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester

4-{5-[bis-(2-chloro-ethyl)amino]-1-methyl-1H-benzoimidazol-2-yl}butyric acid ethyl ester

Conditions
ConditionsYield
Stage #1: chloroacetic acid; ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
Stage #2: With borane-THF In tetrahydrofuran at 55 - 58℃; for 1.83333h;
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoate‐2,2,4,4‐d4

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoate‐2,2,4,4‐d4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen chloride; water-d2; water / 1.5 h / 180 °C / Microwave irradiation; Sealed tube
2: thionyl chloride / 4.5 h / 0 - 50 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

ethyl 4‐(5‐(bis (2‐hydroxyethyl)amino)‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoate‐2,2,4,4‐d4

ethyl 4‐(5‐(bis (2‐hydroxyethyl)amino)‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoate‐2,2,4,4‐d4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen chloride; water-d2; water / 1.5 h / 180 °C / Microwave irradiation; Sealed tube
2: thionyl chloride / 4.5 h / 0 - 50 °C
3: acetic acid / water-d2 / 19 h / 0 - 25 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

C18H19(2)H6Cl2N3O2

C18H19(2)H6Cl2N3O2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen chloride; water-d2; water / 1.5 h / 180 °C / Microwave irradiation; Sealed tube
2: thionyl chloride / 4.5 h / 0 - 50 °C
3: acetic acid / water-d2 / 19 h / 0 - 25 °C
4: thionyl chloride / dichloromethane / 10 h / 0 - 25 °C
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

4‐(5‐(bis(2‐chloroethyl)amino)‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoic‐2,2,4,4‐d4 acid hydrochloride

4‐(5‐(bis(2‐chloroethyl)amino)‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoic‐2,2,4,4‐d4 acid hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogen chloride; water-d2; water / 1.5 h / 180 °C / Microwave irradiation; Sealed tube
2: thionyl chloride / 4.5 h / 0 - 50 °C
3: acetic acid / water-d2 / 19 h / 0 - 25 °C
4: thionyl chloride / dichloromethane / 10 h / 0 - 25 °C
5: hydrogen chloride; water / water-d2 / 2 h / Reflux
View Scheme
2-(2-Chloroethoxy)ethanol
628-89-7

2-(2-Chloroethoxy)ethanol

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

C18H27N3O4

C18H27N3O4

Conditions
ConditionsYield
With sodium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃;
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

C20H31N3O5

C20H31N3O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate; potassium iodide / N,N-dimethyl-formamide / 80 °C
2: acetic acid / water / 24 h / 5 - 10 °C / Sealed tube
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate; potassium iodide / N,N-dimethyl-formamide / 80 °C
2: sodium ethanolate / ethanol / 48 h / 0 - 10 °C / Sealed tube
View Scheme
Multi-step reaction with 2 steps
1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 85 °C
2: acetic acid / water / 24 h / 5 - 10 °C / Sealed tube
View Scheme
Multi-step reaction with 2 steps
1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 85 °C
2: sodium ethanolate / ethanol / 48 h / 0 - 10 °C / Sealed tube
View Scheme
ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate
3543-73-5

ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate

C18H25Cl2N3O3*ClH

C18H25Cl2N3O3*ClH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium carbonate; potassium iodide / N,N-dimethyl-formamide / 80 °C
2.1: acetic acid / water / 24 h / 5 - 10 °C / Sealed tube
3.1: thionyl chloride; chloroform / chloroform / 0 - 50 °C
3.2: 80 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium carbonate; potassium iodide / N,N-dimethyl-formamide / 80 °C
2.1: sodium ethanolate / ethanol / 48 h / 0 - 10 °C / Sealed tube
3.1: thionyl chloride; chloroform / chloroform / 0 - 50 °C
3.2: 80 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 85 °C
2.1: acetic acid / water / 24 h / 5 - 10 °C / Sealed tube
3.1: thionyl chloride; chloroform / chloroform / 0 - 50 °C
3.2: 80 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 85 °C
2.1: sodium ethanolate / ethanol / 48 h / 0 - 10 °C / Sealed tube
3.1: thionyl chloride; chloroform / chloroform / 0 - 50 °C
3.2: 80 °C
View Scheme

1-Methyl-5-amino-1H-benzimidazole-2-butanoic acid ethyl ester Specification

The 1-Methyl-5-amino-1H-benzimidazole-2-butanoic acid ethyl ester is an organic compound with the formula C14H19N3O2. The systematic name of this chemical is ethyl 4-(5-amino-1-methyl-benzimidazol-2-yl)butanoate. With the CAS registry number 3543-73-5, it is also named as 1H-benzimidazole-2-butanoic acid, 5-amino-1-methyl-, ethyl ester.

The other characteristics of 1-Methyl-5-amino-1H-benzimidazole-2-butanoic acid ethyl ester can be summarized as: (1)ACD/LogP: 1.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.69; (4)ACD/LogD (pH 7.4): 1.67; (5)#H bond acceptors: 5; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 7; (8)Polar Surface Area: 70.14 Å2; (9)Index of Refraction: 1.59; (10)Molar Refractivity: 72.76 cm3; (11)Molar Volume: 215.3 cm3; (12)Polarizability: 28.84×10-24 cm3; (13)Surface Tension: 44.5 dyne/cm; (14)Density: 1.21 g/cm3; (15)Flash Point: 239 °C; (16)Enthalpy of Vaporization: 73.43 kJ/mol; (17)Boiling Point: 471.6 °C at 760 mmHg; (18)Vapour Pressure: 4.61E-09 mmHg at 25°C.

People can use the following data to convert to the molecule structure. 
1. SMILES:CCOC(=O)CCCc1nc2cc(ccc2n1C)N
2. InChI:InChI=1/C14H19N3O2/c1-3-19-14(18)6-4-5-13-16-11-9-10(15)7-8-12(11)17(13)2/h7-9H,3-6,15H2,1-2H3 
3. InChIKey:JUMGOLYNZBZPKE-UHFFFAOYAM
4. Std. InChI:InChI=1S/C14H19N3O2/c1-3-19-14(18)6-4-5-13-16-11-9-10(15)7-8-12(11)17(13)2/h7-9H,3-6,15H2,1-2H3
5. Std. InChIKey:JUMGOLYNZBZPKE-UHFFFAOYSA-N

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