Disodium disulfite → 6-[[1-Phenyl-2-(phenylmethanesulfonyl)-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

HRID 1070876Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16](SCC3C=CC=CC=3)[N:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]=2[CH:32]=1.Cl[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41](OO)=O)[CH:36]=1.[S:45]([O:48]S([O-])=O)([O-])=[O:46].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([S:45]([CH2:41][C:37]3[CH:36]=[CH:35][CH:40]=[CH:39][CH:38]=3)(=[O:48])=[O:46])[N:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]=2[CH:32]=1

Participants

Conditions

Temperature: 20 °C

Procedure

300 mg of 6-[(2-benzylmercapto-1-phenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid methyl ester was dissolved in 6 ml of dichloromethane, mixed with 468 mg of m-chloroperbenzoic acid (about 60%), and the mixture was stirred for 48 hours at 20° C. It was mixed with sodium disulfite solution, extracted twice with dichloromethane, the combined organic phases were washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 179 mg was obtained.

Workup

extractionextracted twice with dichloromethane
washthe combined organic phases were washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
customdried on sodium sulfate
concentrationconcentrated by evaporation in a vacuum
customThe residue was purified by column chromatography on silica gel
custom179 mg was obtained

Sources & evidence

ORD record: ord-e30ef26206f94f6d9b0c096e51fee573
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903126B2

Reaction notes

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