Beta-Alanine → 4-(2-nitro-1-propenyl)phenyl-1H-imidazole

Participants

Reaction Steps

A mixture of 292 g (1.70 mole) of 4-(1H-imidazol-1-yl)benzaldehyde, 153.7 g (1.97 mole) of nitroethane (96%), and 15.4 g (.173 mole) of β-alanine in 1000 ml n-butanol is refluxed for nine hours. The reaction mixture is allowed to cool overnight, the solid collected, and washed successively with ether and water to give 78.7 g of dark yellow crystals, mp 119°-120° C. Concentration of the filtrate to approximately 500 ml and cooling at 0° gave a second crop (87.2 g) of the product, mp 116°-118° C.

Provenance & Evidence