Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-methylbenzonitrile | HCID 58200108 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178423542 | HCID 178423542 | — |
Reaction Steps
Hydroxylamine hydrochloride (0.27 g) was added to a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzonitrile (1.1 g) (Example I4) and triethylamine (0.65 ml) in ethanol (30 ml). The reaction mixture was heated to 85° C. for 20 hours. The reaction mixture was allowed to cool to ambient temperature before adding more hydroxylamine hydrochloride (0.078 g). The reaction mixture was again heated to 85° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to give Compound No. A1 of Table A (0.84 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08193221B2 |
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| Source dataset | uspto-grants-2012_06 |
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| ORD ID | ord-e47d3076d5e747958bac0ec92f5418a5 |
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| Source note | uspto-grants-2012_06 |
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