SYNTHESIS OF 4′-NITROPHENYL-BENZTHIAZOL- 6-YL SULFIDES AND 4′-NITROPHENYL- BENZTHIAZOL-6-YL SULFONES CONTAINING THIAZOLIDINONES

Abstract

2-Amino-6 (p-nitrophenylthio)benzthiazol (1) reacted with carbon disulfide in the presence of aqueous sodium hydroxide in N,N-dimethylformamide as solvent, to form the sodium salt of the dithiocarbon imidic acid. Without further purification, this salt was alkylated with sodium chloroacetate and treated with HCl to give the corresponding thiazolidinone (2). The thiazolidinone (2) underwent oxidation to the corresponding sulfone (3) when treated with AcOH/H₂O₂ and condensed easily with aromatic aldehydes, to give the corresponding 5-arylidinethiazolidinones (4), which after oxidation with H₂O₂,/ AcOH gave the sulfones (7). Sulfone (3), condensed with aromatic aldehydes, led to the same com pounds (7). Thiazolidinone (2) reacted with either one or two equivalents of an aromatic amine pro ducing compounds 5 and 6, respectively. The latter were oxidized with H₂O,/AcOH to give the sulfones 8 and 9.

Key Words:

• Synthesis
• thiazolodiaryl sulfides and diarylsulfones
• arylthiobenzthiazol and thiazolidinones.