| Abstract: | Synthesis and Structure Elucidation of Sulfamoyl Guanidines A series of sulfamoyl guanidines 2a--hyphen;p and 4 was synthesized by addition of sulfurylchloride to dialkylcyanoamides and subsequent aminolysis of the N,N-dialkyl-N′-chlorosulfonyl-chloroformamidines with primary or secondary amines. Advantageously, the aminolysis can be performed with trimethylsilylamines as amine component by continuous withdrawing of the formed trimethylchlorosilane. Phase transfer catalyzed methylation led to a specific alkylation of the sulfamoyl group to form the 2-(aryl-methyl-sulfamoyl)-guanidines ( 5a--hyphen;5g, 5h ). All compounds were characterized by m.s.-, i.r.-, 1H-n.m.r.- and 13C-n.m.r.-spectra. I.r. and 1H-n.m.r. data show the existence of an intramolecular hydrogen bonding between the guanidine NH group and the SO2 group. |
