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

HRID 1070848
Notes
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Reaction equation

HRID 1070848 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24346Disodium disulfiteHCID 70297m-Chloroperbenzoic acidHCID 102234206-[[1-phenyl-2-propylmercapto-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

Product 1

HCID 101384106-[[1-Phenyl-2-propanesulfonyl-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

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

  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
  6. custom30 mg was obtained

Sources & evidence

ORD record
ord-46fcf42c1d3f4cdb9e3d26319a5ecce6
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06903126B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes