Hydrochloric Acid → 2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid

HRID 23910Notes

Reaction equation

HRID 23910 reaction equation
C[O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]2[N:9]([CH3:22])[C:10]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO.O>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:10]2[N:9]([CH3:22])[C:8]3[CH:23]=[CH:24][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)=[CH:15][CH:16]=1)#[N:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15516401HCID 15516401, compound

Product 1

HCID 155164022-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5.0 g of 2-[2-(4-Cyanophenyl)-ethyl]-1-methyl-benzimidazole-5-yl-carboxylic acid-methyl ester (15.7 mmol) are dissolved in 50 ml of methanol, treated with 20 ml of an aqueous sodium hydroxide solution(1 N) and boiled under reflux for 0.5 hours. It is then treated with 20 ml of an aqueous solution of hydrochloric acid (1 N) and diluted with water. The precipitated crystals are filtered off, and washed with water, acetone and ether. The raw product obtained is re-crystallized from dimethyl formamide. Yield: 4.5 g (94%); MPt.: >220° C.

Workup

  1. temperatureunder reflux for 0.5 hours
  2. filtrationThe precipitated crystals are filtered off
  3. washwashed with water, acetone and ether

Sources & evidence

ORD record
ord-e9b40806e27e49bd846d9ffbfa6c5c49
Source dataset
uspto-grants-2005_02
Patent number
US06855713B2

Reaction notes

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