Ethanol → HCID 14076670, compound

Participants

Reaction Steps

To a suspension of 2.15 (0.085 mole) of sodium hydride in 200 ml dimethylformamide is added 29.1 g (0.075 mole) of 3-{2-nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-N,N-dimethylpropanamide in in 50 ml dimethylformamide at such a rate that excessive foaming is avoided. To the resulting suspension, stirred in a nitrogen atmosphere, is added 14.2 g (0.10 mole) of methyl iodide to give a reaction mixture, which is stirred at room temperature overnight. The reaction mixture is then treated with 5 ml of ethanol, poured into 1-liter of water and extracted with ether. The resulting ether solution is washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to obtain a residual oil which is chromatographed on Silicar® CC-7. Elution with chloroform gives a major fraction consisting of 16 g which is recrystallized from hexane to give 3-{2-nitro-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl}-N,N-dimethylpropanamide having a melting point of 51° -54°.

Provenance & Evidence