Pyridine → HCID 70574507, compound

Participants

Reaction Steps

A reaction flask was charged with 3.9 g (0.011 mole) of 2-amino-4-(4-chlorophenylcarbamoylethylidene) thiazole hydrobromide (M.P. 112°-16°; prepared from 4-bromo-4'-chloro-2-methylacetoacetanilide and thiourea in ethanol), 30 ml of pyridine and 1.1 g (0.018 mole) of methyl isocyanate. The solution was allowed to stir overnight at ambient temperature. On the following morning, the pyridine solution was poured into water. The water was decanted from the residual oil. With stirring, the addition of fresh water caused the residue to solidify. The solid was dissolved in hot ethanol. The crystalline material in the cooled mixture was collected on a vacuum filter. There was obtained 1.4 g (38%) of white solid, M.P. 203°-205°. N.M.R. (dimethyl-d6 sulfoxide, CDCl3) ∂1.3-1.6 (CH3, doublet), 2.5-2.8 (NCH3, doublet), 3.5-3.8 (CH), 6.5 (hetero-aromatic), 7.1-7.7 (aromatic), 9.9 and 10.4 [NHC(O)NH].

Provenance & Evidence