Ammonium Chloride → 1,2-Benzisothiazol-5-amine, 3-chloro-

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 3-chloro-5-nitrobenzo[d]isothiazole (4.53 g, 21.1 mmol), iron (7.2 g, 129 mmol) and ammonium chloride (2.4 g, 45 mmol) in ethanol/water (2:1, 270 mL) is allowed to stir at 80° C. for 1.5 h. The resulting dark reaction mixture was filtered through Celite while still hot and concentrated under reduced pressure to give a brown solid, which was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and brine. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a brown solid which was triturated with hexanes to provide 3-chlorobenzo[d]isothiazol-5-amine (3.7 g) as a yellow solid. 1H NMR (300 MHz, CDCl3): 7.57 (dd, 1H), 6.99 (dd, 1H), 6.66 ppm (dd, 1H). MW=184 confirmed by LC-MS, tr=10.41 min (Method Y) MH+=185.

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