Sodium Thiosulfate → HCID 68664058, compound

HRID 452751Notes

Reaction equation

HRID 452751 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[CH:13][N:12]([C:15]4[CH:20]=[CH:19][C:18](SC)=[CH:17][CH:16]=4)[C:11]=3[CH:23]=2)=[N:4][N:3]=1.Cl[C:25]1C=CC=C(C(OO)=O)C=1.[S:35]([O-:39])([O-])(=[O:37])=S.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[CH:13][N:12]([C:15]4[CH:20]=[CH:19][C:18]([S:35]([CH3:25])(=[O:39])=[O:37])=[CH:17][CH:16]=4)[C:11]=3[CH:23]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 44482295HCID 44482295, compound

Product 1

HCID 68664058HCID 68664058, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[4-(methylthio)phenyl]-1H-benzimidazole (322 mg, 1.00 mmol) in dichloromethane (10 mL) was added m-chloroperbenzoic acid (479 mg, 2.00 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 1 hr. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred for 1 hr. The organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1-0/1), and recrystallized from hexane/chloroform to give the title compound (302 mg, yield 85%) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-db9737aae24d4267b2b77b2dc90abbf9
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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