Water → N-[2-(3,5-dichloropyridin-2-yl)-2-(sec-butoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a suspension of 500 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide and 352 mg of potassium carbonate in 1.3 ml of N,N-dimethylformamide, 704 mg of 2-iodobutane was added, and the mixture was stirred at room temperature for 12 hours. After completion the reaction, the reaction mixture was mixed with 3 ml of water and extracted with ethyl acetate (3 ml×2), the resulting organic layers were combined, washed with water (3 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 50:50) as the eluent to obtain 522 mg of the desired product as a pale yellow resinous substance.

Provenance & Evidence