Dimethyl Sulfate → 3-(4,5-Dimethoxy-2-methylaminophenyl)-2-methyl-2-propenic acid phenethyl amide

Participants

Reaction Steps

To a nonaqueous ether solution of 3.00 g (8.81 mmol) (E) 3-(2-amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid phenethyl amide and 1.34 ml (9.69 mmol) of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.), 0.92 ml (9.69 mmol) of dimethyl sulfate (manufactured by Wako Pure Chemical Industries, Ltd.) was slowly added dropwise. Thereafter, reflux was carried out for 2 hours at 34° C. to 35° C. After the completion of the reaction, the solvent was evaporated, and the resulting residue was dissolved in ethyl acetate. Thus obtained ethyl acetate layer was washed with water and was dried with sodium sulfate. The dried solution was concentrated under a reduced pressure, and the resulting crude product was refined by an aminopropyl-modified type silica gel column chromatography (n-hexane/ethyl acetate=1/1), whereby 1.12 g of the aimed compound was obtained as a yellowish crystal (yield: 35.9%).

Provenance & Evidence