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

Participants

Reaction Steps

To a suspension of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide (5) (22.07 g, 95 mmol) in anhydrous dimethylformamide (114 mL) under nitrogen in an ice bath is added sodium hydride (Aldrich, 60% in mineral oil) (4.75 g, 119 mmol) and, within 15 minutes, the gas evolution has ceased. To the above reaction mixture is added a solution of methyl iodide (Aldrich) (14.2 g, 99.8 mmol). The reaction mixture is stirred overnight and allowed to warm to room temperature. The reaction is triturated with hexane (3×150 mL) which is discarded. The reaction mixture is poured into ice water, extracted with dichloromethane (3×200 mL) which is dried with anhydrous sodium sulfate. The dry dichloromethane is concentrated to yield a solid, which is triturated with a solution of ethyl acetate and hexane (1:1, 200 m l). Product (6) is obtained as an orange solid (16.9 g, 68.6 mmol, 72%).

Provenance & Evidence