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

HRID 460518Notes

Reaction equation

HRID 460518 reaction equation
[CH3:1][O:2][C:3](=[O:34])[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][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:15]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:14]=2[CH:33]=1.ClC1C=CC=C(C(OO)=[O:43])C=1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:34])[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][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:43])[N:15]([C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[C:14]=2[CH:33]=1

Participants

5

Reactant 3

HCID 24346Disodium disulfiteHCID 70297m-Chloroperbenzoic acidHCID 101625126-[[2-Benzylmercapto-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]Hexanoic Acid Methyl Ester

Product 1

HCID 103000816-[[1-(4-methylphenyl)-2-(phenylmethanesulfinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl esterYield 44.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

500 mg of 6-[[2-benzylmercapto-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was dissolved in 9 ml of dichloromethane, mixed with 303 mg of m-chloroperbenzoic acid (about 60%), and the mixture was stirred for 2 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. 232 mg of 6-[[1-(4-methylphenyl)-2-(phenylmethanesulfinyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was obtained.

Workup

  1. extractionextracted twice with dichloromethane
  2. washthe combined organic phases were washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-53af1c8c71eb4a9e8d77ba4c9521f8b6
Source dataset
uspto-grants-2007_03
Patent number
US07196202B2

Reaction notes

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