Dichloromethane → HCID 68663919, compound

HRID 452666Notes

Reaction equation

HRID 452666 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:20][C:21](SC)=[N:22][N:23]=4)[CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1.ClCCl.Cl[C:31]1C=CC=C(C(OO)=O)C=1.[S:41]([O-:45])([O-])(=[O:43])=S.[Na+].[Na+]>CN(C)C(=O)C>[F:26][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[C:16]([C:19]4[O:20][C:21]([S:41]([CH3:31])(=[O:45])=[O:43])=[N:22][N:23]=4)[CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68663323HCID 68663323, compound

Product 1

HCID 68663919HCID 68663919, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-[4-(difluoromethoxy)phenyl]-6-[5-(methylthio)-1,3,4-oxadiazol-2-yl]-1H-benzimidazole (3.22 g, 8.60 mmol), dichloromethane (24 mL) and N,N-dimethylacetamide (24 mL) was added m-chloroperbenzoic acid (5.15 g, 21.5 mmol), and the resulting mixture was stirred at 50° C. overnight. 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=2/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (2.23 g, yield 64%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed 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 silica gel column chromatography (hexane/ethyl acetate=2/1-0/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-468c6799c22249a1b4d08d8dacabf9cb
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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