Octylamine → 2-Propenamide, N-octyl-

Participants

Reaction Conditions

Reaction Steps

A 500 ml four-necked flask equipped with a thermometer, mechanical stirrer, calcium sulfate-filled drying tube, and pressure-equalizing addition funnel is charged with a solution of 45.3 g of acryloyl chloride (0.5 mole) in 180 g of dichloromethane. The solution is cooled to 0° C. and to it is then slowly added a mixture of 66.6 g of n-octylamine (0.5 mole), 50.6 g of triethylamine (0.5 mole), and 125 g of dichloromethane, over a period of 2.5 hrs., at such a rate that the temperature does not exceed 5° C. Upon completion of the addition, the mixture is allowed to warm gradually to ambient temperature. The product is then stored at -15° C. overnight to complete crystallization of the byproduct triethylamine hydrochloride. After removal of the salt by filtration, the filtrate is washed successfully with 250 g of deionized water. The product is then dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to afford 85 g of N-(n-octyl)acrylamide, bp. 119°-120° (3 mm).

Provenance & Evidence