Acetic Acid → N-(2-aminophenyl)-5-phenyl-4-isothiazolin-3-one

Participants

Reaction Steps

A mixture of 0.560 g (1.880 mmol) N-(2-nitrophenyl)-5-phenyl-4-isothiazolin-3-one, 0.450 g (excess) iron powder, 1 mL glacial acetic acid and 15 mL absolute ethanol was stirred at reflux for one hour. The mixture was allowed to cool to room temperature, poured into 150 mL water and extracted with three 100 mL portions of ethyl acetate. The organic layers were combined, dried, filtered and solvent was evaporated. The resulting solid was recrystallized from ethanol/water to provide 0.250 g (0.930 mmol, 49%) N-(2-aminophenyl) -5-phenyl-4-isothiazolin-3-one, mp=145°-146° C.- NMR (CDCl13 /TMS): 4.15 (bs, 2H), 6.6 (s, 1H), 6.8-7.6 (m, 9H). IR (Nujol): 3358, 3216, 1658. High resolution mass spectrum: Calculated; 269. 074860. Measured; 269.074265. Anal. calcd. for C15H12N2OS: C 67.14, H 4.51, N 10.44, S 11.95; Found C 66.76, H 4.43, N 10.19, S 12.09.

Provenance & Evidence