Chloroform → HCID 178510970, compound

Participants

Reaction Conditions

Reaction Steps

In 24 ml of dimethylsulfoxide was added 4.9 g of sodium cyanide, and the obtained mixture was heated at 70° C. Under stirring, 19.5 g of 2-guanidino-4-(4-chlorobutyl)thiazole was added to the solution at 70° to 75° C., and the solution was stirred at the same temperature for 3 hours. The reaction solution was cooled, and 100 ml of chloroform was added to the solution. After filtering off the undissolved material, the residue was purified by a silica gel column chromatography using a mixture of chloroform and methanol as the developing solvent to provide 15 g of 2-guanidino-4-(4-cyanobutyl)thiazole. The product shows a melting point of 104°-105° C. after recrystallization from a mixture of ethyl acetate and n-hexane. ##STR53## 10 g of 2-guanidino-4-(4-cyanobutyl)thiazole was suspended in a mixture of 60 ml of methanol and 110 ml of chloroform, and hydrogen chloride gas was passed through the solution under stirring at -5° to 5° C. for 2 hours. The resulting solution was allowed to stand at 5° C. for 2 days and the solvent was distilled off. The residue was suspended in a mixture of chloroform and methanol, and the suspension was poured into ice water containing 60 g of potasium carbonate. The chloroform layer was separated, and the aqueous layer was extracted further three times each time with 150 ml of chloroform. The extracts were combined, and dried over anhydrous potassium carbonate. The solvent was distilled off to provide 11 g of methyl 5-(2-guanidinothiazol-4-yl)pentanoimidate having a melting point of 143°-145° C.

Provenance & Evidence