1,6-Dichlorohexan-2-one → 2-Guanidino-4-(4-chlorobutyl)thiazol hydrochloride

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Reaction Steps

In 200 ml of acetone solution of 23.5 g of 1,6-dichloro-2-hexanone was added 16.4 g of guanylthiourea and the solution was stirred for two days. The solvent distilled away and the residue was purified by a silica gel column chromatography using a mixture of chloroform and methanol as the developing solvent to provide 2-guanidino-4-(4-chlorobutyl)thiazol hydrochloride (this product shows a melting point of 113° to 114° C. after the recrystallization from a mixture of ethanol and ether). This hydrochloride was dissolved in 300 ml of water, and to the solution was added 100 ml aqueous solution of 17.4 g of potassium carbonate. The obtained solution was extracted three times each time with 500 ml, 200 ml and 200 ml of chloroform. The extracted solution was combined and dried over anhydrous potassium carbonate and the solvent was distilled away. The obtained crystals were recrystallized from a mixture of ether and n-hexane to provide 20 g of 2-guanidino-4-(4-chlorobutyl)thiazole having a melting point of 83° to 84° C. ##STR52##

Provenance & Evidence