Synthese und Strukturermittlung von Sulfamoyl‐guanidinen

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.