N-(tert-Butyl)thiourea → Methyl 2-[(1,1-dimethylethyl)amino]-5-(2-chlorophenyl)-4-thiazolecarboxylate

Participants

Reaction Steps

A reaction vessel was charged with 50 ml methanol and 4 g (30 mmol) of tert-butyl thiourea. With this mixture stirred and cooled in an ice bath, there was added over a 5-minute period 7.41 g of (30 mmol) methyl 3-chloro-3-(o-chlorophenyl)pyruvate. The reaction mixture was refluxed for 16 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure to yield 9.18 g of a yellow solid which became a hard, glass-like material. This material was recrystallized from an acetone-water solution to yield 7.0 g of a yellow solid product (m.p.=159°-161° C.) identified in Table I.

Provenance & Evidence