Selective Formation of 2, 4- Dinitrothiophenol, and 5- Nitrobenzothiazol by Decomposition of 2, 4-Dinitrochlorobenzene-Dimethylthioformamide Adduct

Abstract

The reaction of 2, 4-dinitrochlorobenzene (DNC) with the excess of dimethylthioformamide (DMTF) at 50°C gave N, N-dimethyl (dinitrophenylthio) methaneiminium chloride (1) as 1 : 1 adduct. Methanolysis of 1 gave 2, 4-dinitrothiophenol (2) at 20°C and gave bis (2, 4-dinitrophenyl) disulfide (3) at 50°C. Thermolysis of 1 suspended in xylene afforded 5-nitroben, zothiazol (5) in the presence of DMTF. Each product was selectively obtained in high yield.