Hydrochloric Acid → 2-Amino-5-chlorobenzenethiol

Participants

Reaction Steps

A solution of 6-chloro-benzothiazol-2-ylamine (Example 200, 17.8 g, 96.7 mmol) and KOH (EM, 87 g, 1.55 mol) in 150 mL of water was refluxed for 2 d. The mixture was cooled to room temperature and was diluted with ice. The solution was brought to pH 5 with concentrated HCl. The mixture was extracted 3× with EtOAc (300 mL). The organic layers were combined and washed twice with a brine solution (300 mL), dried over Na2SO4. Removal of the solvent under reduced pressure gave 10.5 g product. 1H NMR (400 MHz, DMSO) δ 7.20 (d, J=2.5 Hz, 1H), 6.93 (dd, J=8.6, 2.5 Hz, 1H), 6.69 (d, J=8.6 Hz, 1H) 5.30 (s, 3H). MS (EI): m/z 160 (M+H).

Provenance & Evidence