Acrylic Acid → N-Propylacetamide

Participants

Reaction Steps

Acrylic acid (20 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (30 g) were dissolved in water (300 mL). Then aminohydroxybutyric acid (2.0 g) was added to the obtained solution and reacted at room temperature for 10 hours. After the completion of the reaction, water was distilled off and the residue was sufficiently washed with hexane (200 mL) in 3 portions. Next, this residue was dissolved in dimethyl-formamide (350 mL), in which N-hydroxysuccinimide (3 g) and N,N′-dicyclohexylcarbodiimide (3 g) had been dissolved, and reacted overnight. After the completion of the reaction, the solvent was distilled off. Ethyl acetate was added to the residue thus obtained and the precipitate thus formed was filtered off. The filtrate was recovered and a fraction containing the target product was taken up by silica gel column chromatography with the use of ethyl acetate as a mobile phase and alumina column chromatography. Next, a half of the solvent was distilled off with an evaporator and recrystallization was carried out by adding a hexane solvent at −20° C. to thereby give the target monomers (N-propylacetamide, N-propyl acrylamide) (yield: 68%).

Provenance & Evidence