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ChemicalBook CAS DataBase List N-(2-Bromo-thiazol-4-yl)-2,2,2-trifluoro-acetamide

N-(2-Bromo-thiazol-4-yl)-2,2,2-trifluoro-acetamide synthesis

3synthesis methods
-

Yield:-

Reaction Conditions:

with pyridine in dichloromethane;trifluoroacetic anhydride;

Steps:

4 2-Bromo-4-trifluoroacetamidothiazole

EXAMPLE 4 2-Bromo-4-trifluoroacetamidothiazole 4-Amino-2-bromothiazole hydrobromide (19.5 g, 75 mM) was suspended in trifluoroacetic anhydride (200 ml) and dichloromethane (200 ml.). The mixture was cooled to 0° C. and treated dropwise with pyridine (50 ml.). After the addition was complete the mixture was stirred for 1 hour at room temperature, then poured onto a mixture of ice cold 20% aqueous sodium acetate solution (1l) and dichloromethane (500 ml.). The layers were separated and the aqueous layer extracted with dichloromethane (500 ml.). The combined organic layers were dried (MgSO4) and the solvent removed under reduced pressure. Distillation of the residue gave the title compound (18 g, 87%) b.p. 90°-95° C. at 0.3 mm as an oil which subsequently solidified. Sublimation (50°-60° C. at 0.01 mm) gave analytically pure material mp. 71° C. (Found: C, 22.1; H, 0.8; N, 10.2. C5 H2 ON2 BrF3 S requires: C, 21.8; H, 0.7; N, 10.2%).

References:

US4148904,1979,A