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

Participants

Reaction Steps

A solution of 4.62 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide in 25 ml of dimethylformamide was stirred in an inert atmosphere and 1.0 g of sodium hydride (60% oil suspension) was added. After stirring for 1 hour, the liberation of hydrogen had ceased and a solution of 3.0 g of methyl iodide in 10 ml of dimethylformamide was gradually added (with cooling, if necessary). After stirring for an additional 1 hour at room temperature, any volatiles were removed at reduced pressure and then the reaction mixture was triturated 3 times with 100 ml of hexane. The reaction mixture was carefully poured into cold water and extracted exhaustively with methylene chloride. This material was evaporated at reduced pressure to yield a yellow-orange solid. A solution of the crude solid in methylene chloride was passed through a pad of hydrous magnesium silicate. Addition of hexane to the refluxing eluate gave crystals which were collected after cooling. The desired compound was a yellow-orange crystalline material, mp 146°-148° C.

Provenance & Evidence