3-Chloro-4-methylaniline → N-(3-chloro-4-methylphenyl)-5-methyl-4-imidazolecarboxamide

Participants

Reaction Steps

To a solution of 740 g (5.22 moles) of 3-chloro-4-methylaniline and 1054.6 g (10.44 moles) of triethylamine in 10 liters of acetone at room temperature and vigorous stirring, there were added slowly 945 g (5.22 moles) of 5-methyl-4-imidazolecarbonyl chloride hydrochloride. After the addition was ended, the mixture was refluxed for 1 hour and then allowed to cool to room temperature and filtered. The liquid filtrate was evaporated until a slight precipitation appeared, it was then poured over 20 liters of cold water with stirring, filtered and the precipitate was dried to give N-(3-chloro-4-methylphenyl)-5-methyl-4-imidazolecarboxamide, a crude yellowish product. Crystallisation from isopropyl alcohol gave 1108 g (85% yield) of the desired pure product having the same characteristics as the one obtained in Example 1.

Provenance & Evidence