Ethyl cyanoacetate → 2-cyano-N-(4-methylbenzyl)acetamide

Participants

Reaction Steps

A solution of 93 g. (0.825 mole) of ethyl cyanoacetate and 100 g. (0.825 mole) of 4-methylbenzylamine in 150 ml. of 2-methoxyethanol is refluxed for 2 hr. After cooling the solid product is isolated by vacuum filtration, washed with pentane and dried to give 90 g. (57.6%) of amide as a white solid: m.p. 124°-6° C.;ν3220 (NH), 2230 (CN), and 1630 cm.-1 (C= O)δ8.77 broad, 1H, NH); 7.17 (s, 4H, phenyl protons), 4.28 (d, 2H, benzyl methylene), 3.67 (s, 2H, CH2CO), and 2.28 (s, 3H, CH3).

Provenance & Evidence