Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromoacetonitrile | HCID 11534 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 178517507 | HCID 178517507 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59570304 | HCID 59570304 | 72.7% |
Reaction Steps
Into 2 ml of N,N-dimethylformamide was suspended 0.04 g of sodium hydride (60% oily), and 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one was added at room temperature. After stirring for 10 minutes, 0.16 g of bromoacetonitrile was added, and the mixture was stirred for 2 hours. After stirring at 60° C. for 6 hours, the reaction solution was allowed to cool to room temperature, and 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 0.17 g of 4-cyanomethyl-3-(4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (6)).
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-e3d1ba82b89f4fe38bbcd4d0cb1fba8a |
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| Source note | uspto-grants-2012_11 |
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