Water → 1-Methyl-2-[(4-amidinophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-hydroxycarbonylethyl)amide hydrochloride

HRID 2288364Notes

Reaction equation

HRID 2288364 reaction equation
[ClH:1].[CH2:2]([N:5]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[C:6]([C:8]1[CH:28]=[CH:27][C:11]2[N:12]([CH3:26])[C:13]([CH2:15][S:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](=[NH:25])[NH2:24])=[CH:19][CH:18]=3)=[N:14][C:10]=2[CH:9]=1)=[O:7])[CH2:3][CH3:4].[OH-].[Na+].O>C(O)C>[ClH:1].[CH2:2]([N:5]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C:6]([C:8]1[CH:28]=[CH:27][C:11]2[N:12]([CH3:26])[C:13]([CH2:15][S:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](=[NH:24])[NH2:25])=[CH:19][CH:18]=3)=[N:14][C:10]=2[CH:9]=1)=[O:7])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 184124111-methyl-2-[(4-amidinophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride

Product 1

HCID 184126651-Methyl-2-[(4-amidinophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-hydroxycarbonylethyl)amide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.52 g (1.0 mMol) of 1-Methyl-2-[(4-amidinophenyl)-thiomethyl]-benzimidazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)-amide-hydrochloride was dissolved in 15 ml ethanol, mixed with 5 ml of 2N sodium hydroxide solution and stirred for 2 hours at room temperature. Then 5 ml of water were added, the alcohol was distilled off, and it was acidified with concentrated hydrochloric acid. The water was distilled off in vacuo, and the crude product was taken up in 5 ml of ethanol and filtered to remove the insoluble sodium chloride. After the solvent had been distilled off the title compound was obtained as a white solid. Yield: 0.43 g (88% of theory), Rf value: 0.19 (silica gel; ethyl acetate/ethanol/ammonia =50:45:5) C23H27N5O3S (453.57) ##EQU10##

Workup

  1. distillationthe alcohol was distilled off
  2. distillationThe water was distilled off in vacuo
  3. filtrationfiltered
  4. customto remove the insoluble sodium chloride
  5. distillationAfter the solvent had been distilled off the title compound
  6. customwas obtained as a white solid

Sources & evidence

ORD record
ord-eff6ed077cf846709c9197c01b867713
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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