Monosubstituted guanidines from primary amines and aminoiminomethanesulfonic acid

Aminoiminomethanesulfonic acid, H2N-C(NH)SO3H, converts primary amines to the corresponding guanidine derivatives at 20°C. This crystalline reagent is readily prepared by the peracetic acid oxidation of fonnamidinesulfim'c acid, H2N-C(NH)SO2H. The synthesis is illustrated by a representative group of simple monosubstituted guanidines shown in Table I.