Ethyl cyanoacetate → N-(2-chlorobenzyl)-2-cyanoacetamide

Participants

Reaction Steps

A solution of 80.5 g. (0.71 mole) of ethyl cyanoacetate and 100 g. (0.71 mole) of 2-chlorobenzylamine in 200 ml. of absolute ethanol heated at reflux for 2 hours and then allowed to stand at ambient temperature overnight. The solvent is removed in vacuo and the residue is recrystallized from ether/pentane to give 56 g. (38% yield) of the desired product as a near white solid, m.p. 102°-4° C.; ν3300 (NH), 2270 (CN), and 1650 cm.-1 (C= O); δ 8.7 (broad, 1H, NH), 7.35 (broad s, 4H, aromatic protons), 4.40 (d, 2H, benzyl methylene) and 3.7 (broad s, 2H, CH2CO).

Provenance & Evidence