Sodium Carbonate → HCID 85923302, compound

Participants

Reaction Steps

A solution of 15.66 g of phenyl chloroformate in 25 ml of methylene chloride was added to a stirred and ice-cooled solution of 8.21 g of 1-methylimidazole in 175 ml of methylene chloride. To the resulting white suspension was added 7.15 g of 1-methyl-2-(nitromethylene)imidazolidine in portions as a solid. After stirring overnight at room temperature, the reaction mixture was washed twice with water. The organic layer was dried (MgSO4) and concentrated. The residual orange syrup was treated with water, and this mixture allowed to stand at room temperature overnight. The resulting solid was isolated by filtration. Trituration with ethyl acetate gave white powder. Recrystallization from a mixture of 60 ml of dimethyl sulfoxide and 45 ml of water gave 3-methyl-2-(1-nitro-2-oxo-2-phenoxyethylidene)-1-imidazolidinecarboxylic acid phenyl ester (1A), as a white solid, m.p.: 214°-215° C. A heterogeneous mixture of 1.92 g of 1A in 10 ml of dimethyl sulfoxide and 0.55 g of sodium carbonate in 3 ml of water was stirred at room temperature for two days. Crude, solid product was obtained by dilution with 30 ml of water and then filtration. Recrystallization from dimethyl sulfoxide: water yielded 1, as white crystals, m.p.: 234°.

Provenance & Evidence