Reaction between Sulfaguanidine and 1, 3-Ketaldehydes (Synthesis of p-Aminobenzenesulfonamido-methylpyrimidine). I

• Published in: YAKUGAKU ZASSHI Vol. 69; no. 2; pp. 82 - 85
• Main Authors: Sugasawa, Shigehiko, Ban, Yoshio, Mochizuki, Ruriko
• Format: Journal Article
• Language: Japanese; English
• Published: The Pharmaceutical Society of Japan 15.02.1949
• ISSN: 0031-6903; 1347-5231
• DOI: 10.1248/yakushi1947.69.2_82

In order to examine the reactivity of guanidine residue in acetylsulfaguanidine and sulfaguanidine, formylcyclohexanone was applied on the latter two compounds. Acetyl compound easily reacted with formylcyclohexanone in pyridine solution and the objective compound was obtained. In the case of sulfaguanidine, irrespective of the presence of free amino radical in para-position, only the guanidine group reacted giving a dehydrated (1mol. H O) compound in alcoholic solution and dehydrated (2mol. H2O) and cyclized compound under the presence of NaOC2H5 in an alcoholic solution. The acetal obtained by the treatment of Na-formylacetone with alcoholic HCl easily gives sulfamerazine by either heating to 140-150°, under pressure, in alcoholic solution with acetylsulfaguanidine under the presence of NaOC2H5, or by refluxing over a water bath with sulfaguanidine.