Disodium disulfite → 6-[[1-Phenyl-2-propanesulfonyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

HRID 460512Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:29])[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](SCCC)[N:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[CH:28]=1.Cl[C:31]1[CH:36]=CC=C(C(OO)=O)[CH:32]=1.[S:41]([O:44]S([O-])=O)([O-])=[O:42].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:29])[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:41]([CH2:32][CH2:31][CH3:36])(=[O:44])=[O:42])[N:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:14]=2[CH:28]=1

Participants

Conditions

Temperature: 20 °C

Procedure

85 mg of 6-[[1-phenyl-2-propylmercapto-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was dissolved in 2 ml of dichloromethane, mixed with 59 mg of m-chloroperbenzoic acid (about 60%), and the mixture was stirred for 9 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. 30 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
custom30 mg was obtained

Sources & evidence

ORD record: ord-4a74f51dca774f5ab41fea88813af90b
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196202B2

Reaction notes

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