Disodium disulfite → 6-[[1-(4-methylphenyl)-2-propanesulfinyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

HRID 460516Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])[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:18][CH2:19][CH2:20][CH3:21])[N:15]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[C:14]=2[CH:29]=1.ClC1C=CC=C(C(OO)=[O:39])C=1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:30])[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:18]([CH2:19][CH2:20][CH3:21])=[O:39])[N:15]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:14]=2[CH:29]=1

Participants

Conditions

Temperature: 20 °C

Procedure

600 mg of 6-[[1-(4-methylphenyl)-2-propylmercapto-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was dissolved in 10 ml of dichloromethane, mixed with 405 mg of m-chloroperbenzoic acid (about 60%), and the mixture was stirred for 15 minutes 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. 525 mg of 6-[[1-(4-methylphenyl)-2-propanesulfinyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester 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

Sources & evidence

ORD record: ord-e8d615bf03e94ede8ec518153753c954
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196202B2

Reaction notes

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