Aromatic, aliphatic and sterically hindered amines react smoothly with comm
ercially available N,N'-bis-BOC-S-methylisothiourea 2 in the presence of me
rcury chloride to give the protected guanidine in good yield. It is particu
larly noteworthy that 2 can also be employed in a straightforward, two-step
synthesis of monoaryl internal guanidines.