Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | HCID 68664411 | HCID 68664411 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 68662873 | HCID 68662873 | 61% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08492378B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-ef603afccd884d07bebc89618646dfeb |
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| Source note | uspto-grants-2013_07 |
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