Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 178517507 | HCID 178517507 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59570342 | HCID 59570342 | 81.7% |
Reaction Steps
Into 3 ml of tetrahydrofuran was suspended 0.06 g of sodium hydride (60% oily), and 0.3 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one was added at 0° C. The mixture was stirred at room temperature for 10 minutes, 0.22 g of iodomethane and 1 ml of dimethylformamide were added, and the mixture was stirred at 40° C. for 3 hours. Thereafter, the reaction solution was poured into an aqueous saturated ammonium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.26 g of 4-methyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (3)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318776B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-347e79e260ab4894b78f05fd36cfef9a |
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| Source note | uspto-grants-2012_11 |
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