Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | HCID 23114712 | HCID 23114712 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 23114552 | HCID 23114552 | 82.2% |
Reaction Steps
To a methylene chloride (10 ml) solution of N-[5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanesulfonamide (331 mg, 0.696 mmol) was added 3-chloroperbenzoic acid (120 mg, 0.696 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. At the same temperature, 3-chloroperbenzoic acid (60 mg, 0.348 mmol) was added to the reaction mixture. After stirring at 0° C. for 10 minutes, a saturated aqueous solution of sodium thiosulfate was added to the reaction mixture. The resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure. To the residue thus obtained was added ether and the solid thus precipitated was collected by filtration to give the title compound (281 mg, 0.572 mmol, 82%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932271B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-d118dd87dbe3479d9aafbc766b6ea752 |
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| Source note | uspto-grants-2011_04 |
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