4-Chlorobenzylamine → HCID 178470383, compound

Participants

Reaction Steps

A solution of ethyl 2-oximinoacetoacetate (6 g, 38 mmol; obtained according to Org.Synth. 1941, 21, 67) in MeCN (75 mL) was treated with 4-chlorobenzylamine (5.6 g, 40 mmol) at reflux for 18 h. Next, the reaction mixture was allowed to cool and the yellow solid formed was collected by filtration to give ethyl 2-(4-chlorophenyl)-5-methyl-3H-imidazole-4-carboxylate as a white solid (4.1 g, 40%): mp 237°-238° C.; 1H NMR (300 MHz, DMSO--d6) δ (DMSO) 7.96 (d, J=8, 2H, arom), 7.57 (d, J=8, 2H, arom), 4.27 (q, J=7, 2H, OCH2), 2.54 (s, 3H, Me-imidazole), 1.33 (t, J=7, 3H, OCH2CH3). Analysis calculated for C13H13ClN2O2 : C 58.99; H 4.95; N 10.58. Found: C 59.20; H 4.95; N 10.59.

Provenance & Evidence