Three New Thiosaccharin Derivatives Generated in a Complex Reaction System

GUSTAVO A. ECHEVERRÍA ; OSCAR E. PIRO ; JUAN ZINCZUK ; ENRIQUE J. BARAN

Journal of the Argentine Chemical Society

ASOCIACIÓN QUÍMICA ARGENTINA

Lugar: Buenos Aires; Año: 2013

0365-0375

The reaction between thiosaccharin and ethylamine showed to be relatively complex. The main product of this reaction is 3-ethylamino-1,2-benzisothiazole 1,1-dioxide (1), which could be clearly identified by NMR and IR spectroscopies. Ethylammonium thiosaccharinate (2) and 3-vinylamino-1,2-benzisothiazole 1,1 dioxide (3) were generated as minor by products during this reaction and their  structures were determined by X-ray diffraction methods. The (2) salt crystallizes in the monoclinic P21/c space group with a=13.1367(5), b=9.9721(4), c=8.8217(3) Å, β=99.125(4)°, and Z=4, whereas compound (3) belongs to the P21/m space group with a=7.1572(5), b=7.0242(7), c=9.5503(8) Å, β=95.008(7)°, and Z=2.