Benzaldehyde → 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone

Participants

Reaction Steps

A solution of 1-(2,3-dimethylimidazo[2,1-b]thiazole-5-yl ethanone (See procedures from Preparation 6) (Formula D-1) (0.87 g) in THF (25 mL) was treated with benzaldehyde (0.52 mL) and sodium methoxide (0.11 g). After 18 hours trace 1-(2,3-dimethylimidazo[2,1-b]thiazol-5-yl ethanone remained and additional benzaldehyde (0.2 mL) was added. After an additional 2.5 hours the reaction was diluted with ice water and precipitated 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone (FIG. D-2) (1.03 g) was filtered. Crystallization from isopropanol solution gave pure 2,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone (FIG. D-2), m.p. 189-190°.

Provenance & Evidence