SYNTHESIS OF 4′-NITROPHENYL-2-AMINOBENZTHIAZOL-6-YL SULFIDES AND 4′-NITROPHENYL-2–AMINOBENZTHIAZOL-6-YL SULFONES CONTAINING DITHIOCARBAMATE

Abstract

2-Amino-6-[(p-nitrophenyl)thio]benzthiazol (1) reacted with carbon disulfide in the presence of concentrated aqueous sodium hydroxide and with N,N-dimethylformamide as solvent, to form the sodium salt of dithiocarbonimidic acid. This compound was reacted without further purification with one mole of methyl iodide to give monoalkylated product (2). Reaction with two moles of methyl iodide gave the dialkylated product (3). Reaction of (2) with anthranilic acid yielded 2-(2,3-dihydro-2-thioxo4(1H) quinoxa linon-3–yl)-6-[(p-nitrophenyl)thio]benzthiazol (4). Reaction of (3) with ophenylenediamine gave 2-(2-benzimidazolylamino)-6-[(p-nitrophenyl)thio]-benzthiazole (5). And reaction of (3) with potassium salt of anthranilic acid gave 2-(2-imino benzoxazine)+[(pnitrophenyl) thio]benzthiazol (6). (6) was condensed with a range of aromatic amine to form the 3-aryl quinazolinones (7d). Oxidation of compounds (4–7) using H₂O₂ in glacial acetic acid afforded the corresponding diary1 sulfones (8–11).

Key Words:

• Synthesis
• thiazolodiarylsulfides and diarylsulfones, arylthiobenzthiazol and dithiocarbamate.