Methyl iodide → N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-N-methyl-2-(trifluoromethyl)benzamide

Participants

Reaction Steps

To 33 mg of 60% sodium hydride in oil in 5 ml of tetrahydrofuran, 300 mg of the N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide prepared in Step 1 in Synthetic Example 16 in 3 ml of tetrahydrofuran was added dropwise with stirring and cooling with ice, and the mixture was stirred at the same temperature for 30 minutes. Then, the reaction mixture was mixed with 157 mg of methyl iodide, warmed to room temperature and stirred for another 1 hour. After completion of the reaction, the reaction mixture was poured into 20 ml of ice-water and extracted with ethyl acetate (50 ml×1), the organic layer was washed with water (20 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 1:9 to 2:8) as the eluent to obtain 203 mg of the desired product as a pale yellow resinous substance.

Provenance & Evidence