Pyridine → 4-Acrylamido-2-bromothiazole

Participants

Reaction Steps

4-Amino-2-bromothiazole hydrobromide (15.6 g) and acryloylchloride (7 g) were suspended in methylene chloride (100 ml) with stirring and treated with pyridine (16 ml), maintaining reaction temperature at 0° C. with an ice bath. After addition was complete, the reaction mixture was stirred at room temperature for 3 hours, then poured onto 20% aqueous sodium acetate and stirred for 30 minutes. The mixture was filtered and separated and the organic layer washed with 2N hydrochloric acid, water, sodium carbonate solution and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was recrystallised from carbon tetrachloride to give the title compound (0.7 g) m.p. 152°-4° C. (Found: C, 30.5; H, 2.2; N, 11.8. C6H5BrN2OS requires C, 30.9; H, 2.2; N, 12.0%).

Provenance & Evidence