Triethylamine → cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

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Reaction Steps

The solution of 11.5 g thereof in 60 ml of diethyl ether is added dropwise to the mixture of 9.1 g of thionyl chloride, 12.2 g of pyridine and 150 ml of diethyl ether while stirring and cooling with ice. After stirring for 5 minutes at 0°-5°, the mixture is washed with ice-cold N-hydrochloric acid, N aqueous sodium carbonate and saturated aqueous sodium chloride. It is dryed, evaporated, the residue taken up in warm petroleum ether, the solution cooled and the precipitate collected, to yield the 4-methoxycinnamyl chloride melting at 70°-72°. B) To the solution of 11.8 g of 3,4,5-trimethoxyphenylpropiolic acid in 50 ml of tetrahydrofuran, 7.1 g of triethylamine are added while stirring, followed by 50 ml of diethyl ether. The mixture is cooled with ice and to the resulting suspension the solution of 5.4 g of ethyl chloroformate in 25 ml of diethyl ether is added during 5 minutes. The mixture is stirred for 15 minutes at 0°-5°, whereupon the solution of 7.35 g of N-methylcinnamylamine in 35 ml of diethyl ether is added dropwise, followed by 80 ml of methylene chloride. The mixture is stirred for 30 minutes and allowed to warm to room temperature. It is washed with N hydrochloric acid, N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated under reduced pressure, to yield the N cinnamyl-N-methyl --3,4,5-trimethoxyphenylpropiolamide.

Provenance & Evidence