Dimethylformamide → 1H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-

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Reaction Conditions

Reaction Steps

N,N-dimethylformamide (7.04 g, 96.3 mmol) was added to a mixture of 2-n-propyl-3,5-dihydroimidazol-4-one (4.49 g, 35.6 mmol) and POCl3 (14.76 g, 96.3 mmol) in chlorobenzene (40 ml) at 100° C. The mixture was heated for 2 hours at 100° C., cooled and poured on 40 g of ice. The mixture was adjusted to pH 1 by the addition of 30 percent sodium hydroxide solution (22.5 ml) and the phases were separated. The aqueous phase was extracted twice with 40 ml of ethyl acetate each and the combined organic phases were washed with water (20 ml) and filtered on silica gel. After removal of the solvent from the filtrate, 2.79 g of a light brown solid was obtained. Recrystallization from ethyl acetate/petroleum ether yielded the title compound (2.04 g, 33 percent). The product had a melting point of 133.3° to 137.5° C. Other data concerning the product was:

Provenance & Evidence