Cyclohexene → 6-Aminosaccharin

Participants

Reaction Steps

To a solution of 6-nitro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one (11.4 g, 50.0 mmol) and cyclohexene (25.4 mL, 250 mmol) in EtOH (100 mL) was added 5% Pd—C (35 g) at about 0° C. The mixture was refluxed overnight with stirring and then cooled to rt, filtered through Celite® several times until the filtrate became clear. The filtrate was concentrated under reduced pressure. The material was dissolved in saturated aqueous NaHCO3 (200 mL), filtered and to the filtrate was added concentrated hydrochloric acid (pH=7). The precipitate was collected by filtration and washed with water (2×50 mL) to provide 6-amino-1,2-benzisothiazol-3(2H)-one-1,1-dioxide (8.0 g, 68%): 1H NMR (DMSO-d6) δ: 7.61 (s, 1H), 7.59 (s, 1H), 6.95 (d, J=2.0 Hz, 2H), 6.91 (d, J=2.4 Hz, 1H), 6.89 (d, J=2.0 Hz, 1H).

Provenance & Evidence