2-Bromothiazole → HCID 22106696, compound

Participants

Reaction Steps

n-Butyllithium (2.5 M solution in hexanes, 17.3 ml) was added dropwise to a stirred solution of 2-bromothiazole (6.5 g) in anhydrous diethyl ether (40 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylthiazole (5 g) in diethyl ether (10 ml) was added dropwise. After a further 1 hour, the mixture was allowed to warm to room temperature. After 1 hour, saturated aqueous sodium hydrogen carbonate solution was added and the organic phase was separated. Further processing in the usual fashion then gave the title compound. M.p. 146°-147° C. 13C Nmr (CDCl3) 31.4, 76.4, 120.3, 142.0 and 175.2 ppm. Found: C, 45.1; H, 3.5; N, 13.0. C8H8 N2OS2 requires C, 45.2; H, 3.8; N, 13.2%. Hydrochloride, m.p. 137°-140° C. (dec.). 13C Nmr (d6 -DMSO) 28.8, 75.4, 120.6, 142.0 and 176.0 ppm.

Provenance & Evidence