Sulfur Dioxide → HCID 14129246, compound

Participants

Reaction Conditions

Reaction Steps

11.0 g of 5-amino-4-ethoxycarbonyl-1-(2-pyridyl)imidazole was dissolved in 60 ml of conc. hydrochloric acid and the resulting solution was cooled to -5° C. Subsequently, 3.9 g of sodium nitrite was dissolved in 10 ml of water and the resulting solution was added dropwise to the previously prepared solution while maintaining the temperature at -5° C. or lower. After completion of the dropwise addition, the resulting mixture was stirred at the same temperature for 0.5 hour. The thus obtained solution was added dropwise at around 5° C. to 150 ml of a solution of chloroform containing 1.0 g of cuprous chloride and 12 g of sulfur dioxide. After the resulting mixture was stirred at room temperature for 1 hour, was added thereto 300 ml of water and the organic layer was separated. The aqueous layer was extracted with chloroform and the organic layers were combined, washed with water and dried. The solvent was then removed by distillation to give 11.6 g of 5-chloro-4-ethoxycarbonyl-1-(2-pyridyl)imidazole as an oil.

Provenance & Evidence