Hydrochloric Acid → HCID 86654465, compound

Participants

Reaction Steps

In a solution of 1.00 g of 3-(4-amino-3-difluoromethoxyphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in a mixed solution of 10 mL of acetonitrile and 10 mL of water, 5 mL of concentrated hydrochloric acid was added, and a solution of 0.20 g of sodium nitrite in 2 mL of water was added dropwise slowly under cooling with ice and with stirring. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 20 minutes. Then, a solution of 0.47 g of potassium iodide in 1 mL of water was added dropwise carefully. After the completion of the addition dropwise, it was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, 0.041 g of urea was added in the reaction mixture, stirred at room temperature for 30 minutes, then a solution of 0.10 g of sodium sulfite in 5 mL of water was added, and extracted with ethyl acetate (20 mL×2). The combined organic phases were washed with water, and then dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (1:9) to obtain 0.60 g of the aimed product as yellow resinous substance.

Provenance & Evidence