Sodium Thiosulfate → HCID 68663395, compound

HRID 452613Notes

Reaction equation

HRID 452613 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:30])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)=[CH:7][CH:8]=1)=[O:30]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 44482293HCID 44482293, compound

Product 1

HCID 68663395HCID 68663395, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-[4-(methylthio)phenyl]-1H-benzimidazole-6-carboxylate (4.44 g, 14.88 mmol) in dichloromethane (50 mL) was added m-chloroperbenzoic acid (3.07 g, 12.40 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 30 min. Saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred at room temperature for 15 min. The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1-0/1) to give the title compound (3.89 g, yield 83%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=2/1-0/1)

Sources & evidence

ORD record
ord-958ffab6191e44a49ad22cd19376d0f9
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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