Isobutyryl chloride → 2-Bromo-4-isobutyramidothiazole

Participants

Reaction Steps

A solution of isobutyryl chloride (4.15 ml., 40 mM) in pyridine (50 ml.) was cooled to 0° C. and treated portionwise with 4-amino-2-bromothiazole hydrobromide (7.8 g, 30 mM). After stirring for 1 h. the reaction mixture was poured onto 20% aqueous sodium acetate solution (500 ml) and extracted with chloroform (3×200 ml.). The combined organic layers were dried and the solvents removed under reduced pressure to yield an oil which eventually crystallised. Recrystallisation from 60°-80° petroleum ether gave the title compound (2 g, 20%). mp: 95° (Found: C, 34.1; H, 3.8; N, 11.3. C7H9BrN2OS requires C, 33.7; H, 3.6; N, 11.2%).

Provenance & Evidence