N-chlorosuccinamide → N-hydroxy-3-phenyl-4-(trifluoromethyl)isoxazole-5-carbimidoyl chloride

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Reaction Steps

To 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbaldehyde oxime (Intermediate I-12C, 0.34 g, 1.327 mmol) in N,N-dimethylformamide (1 mL) was added N-chlorosuccinamide (0.177 g, 1.327 mmol) in batches over a period of 2 min. at room temperature. The reaction mixture was stirred at room temperature for 30 min. An additional 0.09 g of N-chlorosuccinamide was added in one lot at room temperature and the contents were stirred for 20 min. The reaction mixture was partitioned between ethyl acetate (20 mL) and brine (2×20 mL). The ethyl acetate layer was dried over sodium sulfate and purified by silica gel column chromatography using hexane/ethyl acetate to yield N-hydroxy-3-phenyl-4-(trifluoromethyl)isoxazole-5-carbimidoyl chloride (0.250 g, 0.860 mmol, 64.8% yield) as a white solid. LC/MS M+1=291.2.

Provenance & Evidence