Hydrogen Peroxide → HCID 19921171, compound

HRID 1647886Notes

Reaction equation

HRID 1647886 reaction equation
[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][S:22][CH2:21][CH2:20]3)[C:14]3[CH:25]=[CH:26][C:27]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[O:30])=[CH:28][C:13]=3[N:12]=2)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].[OH:38]O>C(O)(=O)C.C([O-])(=O)C>[ClH:1].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]([CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][S:22](=[O:38])[CH2:21][CH2:20]3)[C:14]3[CH:25]=[CH:26][C:27]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[O:30])=[CH:28][C:13]=3[N:12]=2)=[CH:9][CH:10]=1)(=[NH:3])[NH2:4]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 19921329HCID 19921329, compound

Product 1

HCID 19921171HCID 19921171, compound

Reagents, catalysts & solvents 2

HCID 175AcetateSolventHCID 176Acetic AcidSolvent

Procedure

2.2 g of 2-(4-amidino-phenyl)-5-[(2-methoxycarbonyl-ethyl)-aminocarbonyl]-1-(3-thiomorpholino-propyl)-benzimidazole-hydrochloride are dissolved in 45 ml of glacial acetic acid and a solution of 0.39 ml of 30% hydrogen peroxide in 5 ml of glacial acetate acid is added thereto whilst cooling with ice water. The mixture is stirred for 4 hours whilst cooling with ice and for 16 hours at ambient temperature, the solvent is evaporated off in vacuo and the residue is purified by column chromatography (silica gel; methylene chloride/methanol/water=1:1:0 to 1:1:0.1). Yield: 0.6 g (26% of theory), Rf value: 0.46 (silica gel; methylene chloride/methanol/conc. ammonia=1:1:0.1)

Workup

  1. customthe solvent is evaporated off in vacuo
  2. customthe residue is purified by column chromatography (silica gel; methylene chloride/methanol/water=1:1:0 to 1:1:0.1)

Sources & evidence

ORD record
ord-66eed582e6944b2ba12ad79494881077
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

Loading…