Hydrochloric Acid → 5-Amino-6-chloro-2,1,3-benzothiadiazole

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Reaction Steps

A solution is prepared by dissolving a compound (2) (16.8 g, 0.0779 mol) in methanol (800 mL), and SnCl2.2H2O (87 g, 0.389 mol, 5.0 eq), water (80 mL) and 1N HCl (30 mL) are sequentially put into the solution. The reactant is agitated and reflowed overnight, cooled down to room temperature (24° C.), and condensed under a reduced pressure. The condensate is dissolved in dichloromethane, neutralized with a saturated NaHCO3 aqueous solution, and then passed through Celite. An organic layer is dried and condensed under a reduced pressure so as to obtain a yellow solid-phase compound (3) (13.8 g, yield: 95%). 1H NMR (400 MHz, CDCl3): δ ppm 7.99 (s, 1H), 7.14 (s, 1H), 4.54 (br s, 2H).

Provenance & Evidence