Methyl iodide → N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide

Participants

Reaction Steps

To a suspension of compound 8 (22.07 g, 95 mmol) in anhydrous dimethylformamide (114 mL) under nitrogen in an ice bath was added sodium hydride (4.75 g, 119 mmol, 60% in mineral oil) and, within 15 minutes, the gas evolution had ceased. To the above reaction mixture was added a solution of methyl iodide (14.2 g, 99.8 mmol). The reaction mixture was stirred overnight and allowed to warm to room temperature. The reaction was triturated with hexane (3×150 mL) which was discarded. The reaction mixture was poured into ice water, extracted with dichloromethane (3×200 mL) which was dried with anhydrous sodium sulfate. The dry dichloromethane was concentrated to yield a solid which was triturated with a solution of ethyl acetate and hexane (1:1, 200 mL). Compound 9 was obtained as an orange solid (16.9 g, 68.6 mmol, 72%). GC/MS, m/z=246 at tR=14.63 min (100%). LC/MS, [M+H]′=247.

Provenance & Evidence