Water → HCID 17992063, compound

Participants

Reaction Conditions

Reaction Steps

Butyl lithium (2.4 M, 50 ml) in hexane was added to a solution of 2-chlorothiazole (12.43 g, 0.104 mol) in tetrahydrofuran (400 ml) at -78° C. under at atmosphere of nitrogen. The resultant solution was stirred for 5 minutes before propyl isocyanate (11.25 ml, 0.12 mol) was added and the reaction mixture was then stirred for a further 10 minutes before being hydrolysed with water (100 ml). The solvent was removed under reduced pressure and the residue extracted with ethyl acetate (2×400 ml). The combined organic extract was then washed with saturated sodium chloride solution, dried over magnesium sulphate and the solvent evaporated. Acetic acid (110 ml) was added to the residue and the solution warmed to about 100° C. whereupon zinc dust (11.8 g) was added and the mixture was refluxed for 1 hour. On cooling, the reaction mixture was made basic with ammonium hydroxide and then extracted into ethyl acetate (4×250 ml). The combined organic extract was washed with saturated sodium chloride solution, dried (MgSO4) and then concentrated. Flash chromatography of the residue on a silica gel column using ethyl acetate as eluant gave N-propylthiazole-5-carboxamide (12.2 g) as a pale yellow solid, m.pt. 86° C.

Provenance & Evidence