5-Chloro-2-methylphenyl isothiocyanate → 2-[3-(5-Chloro-2-methylphenyl)-1-phenyl-thioureido]-acetic acid ethyl ester

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Reaction Steps

A mixture of N-phenyl glycine ethyl ester (8.95 g), 5-chloro-2-methylphenyl-isothiocyanate (9.18 g), and chloroform (200 mL) was heated at reflux for 24 hours. The solvent was evaporated. The residue was crystallized from ethyl acetate/hexane mixture. The solid was collected and dried to give 17.2 g of 2-[3-(5-chloro-2-methylphenyl)-1-phenyl-thioureido]-acetic acid ethyl ester as a white solid, m.p. 148°-1500° C. Anal. Calcd. for. C18H19Cl N2O2S: C, 59.58; H, 5.28; N, 7.72. Found: C, 59.79; H, 5.38; N, 7.65. Mass spectrum (EI, M.+) m/z 262/264.

Provenance & Evidence