Study On Processes Of Synthesizing 4(5)-Hydroxymethylimidazole

Processes of synthesizing 4(5)-hydroxymethylimidazole which was very useful in pharmaceutical, insecticide and resin area were studied. Two synthetic routes starting from 1,3-dihydroxyacetone and formamidine acetate as well as imidazole-4,5-dicarboxylic acid as starting material were investigated, and the reductive reaction of ethyl imidazole-4-carboxylate was also investigated.The optimum process starting from 1,3-dihydroxyacetone and formamidine acetate was: 22.54g(0.25mol) 1,3-dihydroxyacetone, 29.12g(0.28mol) formamidine acetate and 120ml isopropanol in liquid ammonia was heated to 40℃ for 8h. The ammonia was evaporated under decreasing pressure, and the precipitate was filtered off and the liquid was poured into hot saturated picric acid solution to get picrate with a yield of 85.0%.The optimum process starting from imidazole-4,5-dicarboxylic acid was: imidazole-4,5-dicarboxylic acid in acetic anhydride was refluxed to get imidazole-4-carboxylic acid, and the product was esterification in ethanol with a catalyzer of concentrated sulfuric acid to get ethyl imidazole-4-carboxylate, at last the compound above was reduced by LiAlH₄ in ether at room temperature to get the target compound, the total yield of this route was 49.6%.