Convenient One-Pot Synthesis of N,N ′-bis(2-Mercaptophenyl)pyridine-2,6-dicarboxamide and N-2-Mercaptophenyl-2′-pyridinecarboxamide Without Protection of the Thiol Group(s)

Abstract

A rapid and convenient procedure for the synthesis of N,N ′-bis(2-mercaptophenyl)pyridine-2,6-dicarboxamide and N-2-mercaptophenyl-2′-pyridinecarboxamide from 2-aminothiophenol and the appropriate acid chloride is reported. The method is compatible only with aromatic acid chlorides containing a heteroatom. Aromatic acid chlorides with no heteroatom yield the corresponding 2-substituted benzothiazoles.

Keywords:

• Carboxamido nitrogen
• Thiol
• Benzothiazole

Acknowledgments

Financial support from NIH (GM 61636) is gratefully acknowledged. K.R. and T.C.H. received support from the NIH-IMSD Grant GM58903.