N-bromobutanimide → 2-Bromomethyl-5-ethoxycarbonyl-4-methylthiazole

Participants

Reaction Steps

A mixture of 5-ethoxycarbonyl-2,4-dimethylthiazole (926 mg), N-bromosuccinimide (890 mg) and benzoyl peroxide (8 mg) in carbon tetrachloride (11 ml) was heated at reflux. After 11/2 h the reaction mixture was allowed to cool and filtered. The filtrate was evaporated and the residual oil diluted with petrol (b.p. 40°-60° C.)-ethyl acetate, 4:1, (5 ml) resulting in the precipitation of a solid. After 1 h the suspension was filtered and the filtrate evaporated to an orange oil. Petrol (2 ml) was added to the oil resulting in the formation of a solid which after cooling was collected to give crystals of 2-bromomethyl-5-ethoxycarbonyl-4-methylthiazole (546 mg), m.p. 48°-58° C., λmax (EtOH) 266 nm (ε 8,640).

Provenance & Evidence