Acetic Acid → N-acetyl-N-(5-amino-benzo[d]isothiazol-3-yl)-acetamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-acetyl-N-(5-nitro-benzo[d]isothiazol-3-yl)-acetamide (1.133 g, 4.06 mmol) in a 1:1 acetic acid:ethyl acetate solution (70 mL) at 50° C. was added iron powder (680 mg, 12.2 mmol). The resulting mixture was stirred at 50° C. for 5 h, then cooled, poured into saturated sodium bicarbonate and extracted into ethyl acetate. The organic layers were combined, washed with water and then brine, dried (MgSO4), filtered, and evaporated. The residue was purified using flash chromatography on silica to afford the desired amine as an orange solid (383 mg, 38%), single spot at Rf 0.30 (1:1 dichloromethane:ethyl acetate). mp 213.0-214.2° C. 1H NMR (CDCl3): δ 8.56 (1H, d, J=9.2 Hz), 7.48 (d, J=2.7 Hz), 7.14 (1H, dd, J=9.2, 2.7 Hz), 2.62 (3H, s), 2.56 (3H, s).

Provenance & Evidence