Acetonitrile → HCID 68662873, compound

HRID 452664Notes

Reaction equation

HRID 452664 reaction equation
CS[C:3]1[O:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[CH:14][N:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=4)[C:12]=3[CH:27]=2)=[N:5][N:4]=1.[C:28](#N)C.ClC1C=CC=C(C(OO)=O)C=1.[S:42]([O-:46])([O-])(=[O:44])=S.[Na+].[Na+]>CN(C)C(=O)C>[CH3:28][S:42]([C:3]1[O:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[CH:14][N:13]([C:16]4[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=4)[C:12]=3[CH:27]=2)=[N:5][N:4]=1)(=[O:46])=[O:44]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 68664411HCID 68664411, compound

Product 1

HCID 68662873HCID 68662873, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 6-[5-(methylthio)-1,3,4-oxadiazol-2-yl]-1-[4-(trifluoromethoxy)phenyl]-1H-benzimidazole (898 mg, 2.29 mmol), acetonitrile (10 mL) and N,N-dimethylacetamide (20 mL) was added m-chloroperbenzoic acid (1.21 g, 5.03 mmol) at room temperature, and the resulting mixture was stirred for 3 days. m-Chloroperbenzoic acid (605 mg, 2.52 mmol) was added to this mixture, and the mixture was further stirred at room temperature for 1 day. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred for 30 min and extracted with ethyl acetate. The organic layer was 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 silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (590 mg, yield 61%) as colorless crystals.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 day
  2. stirringthe mixture was stirred for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ef603afccd884d07bebc89618646dfeb
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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