Hydrochloric Acid → HCID 53745834, compound

Participants

Reaction Steps

A mixture of 1-(2-chloro-5-thiazolylmethyl)-1- phenoxycarbonyl-3-methyl-2-nitroguanidine (Compound No. 6), CH3CN (15 ml) and pyridine (0.55 ml) was cooled to 3°-C. followed by addition of phenyl chlorocarbonate (1.7 ml) in CH3CN (3 ml) below 8° C. over 2 minutes under stirring. After stirring at the same temperature for 1 hour and 25 minutes and then at room temperature for 1 hour, pyridine (0.55 ml) and phenyl chlorocarbonate (1.7 ml) was added to the mixture followed by stirring at room temperature for 1 hour and 15 minutes and at 40° C. for 2 hours. Additional phenyl chlorocarbonate (1.7 ml) was added to the mixture which was stirred for 20 minutes. To the reaction mixture was added CHCl3 (30 ml) and then a mixture of conc. hydrochloric acid (2 ml) and water (8 ml). The reaction mixture was partitioned and the aqueous layer was extracted with CHCl3 (20 ml×3). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The resulting residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (3:2) to afford 0.7 g of 1-(2-chloro-5-thiazolylmethyl)-I,3-diphenoxycarbonyl-3-methyl-2-nitroguanidine (Compound No. 2) as an oil.

Provenance & Evidence