Triethylamine → 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline

Participants

Reaction Steps

A mixture of 3.64 g (0.025 mole) of N-(2-propynyl)-2,6-dimethylbenzenamine and 2.52 g (0.025 mole) of triethylamine in 25 ml of dichloromethane is stirred rapidly under nitrogen at room temperature as 3.06 g (0.025 mole) of 2-furoyl chloride, dissolved in 5 ml of dichloromethane, is added at a moderate rate. Upon addition of the 2-furoyl chloride a vigorous exotherm is noted, causing the solvent to reflux for 2 min. The mixture is stirred for 30 min. and then poured into 200 ml of dichloromethane and washed with water (100 ml), 5% HCl (100 ml), water (100 ml) and brine (100 ml). The organic layer is dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to yield a solid. The solid is washed with n-hexane and vacuum dried to yield 3.65 g (0.0144 mole) of N-(2-furoyl)-N-(2-propynyl)-2,6-dimethylbenzenamine.

Provenance & Evidence