Stannous chloride dihydrate → 1,3-Benzothiazole-2,5-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of ethanol (36 mL) was added 5-nitro-benzothiazol-2-ylamine (Example 15, 78 mg, 0.35 mmol) and tin dichloride dihydrate (449 mg, 2 mmol). The resulting mixture was heated at 80° C. for 4 hours. The solution was cooled to room temperature and the solvent was removed. The residue was dissolved in ethyl acetate and poured onto 50 mL of 1.5 N NaOH solution and extracted using ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to give a solid (43 mg, 66%). 1H NMR (DMSO d) δ: 7.23–7.19 (m, 3H), 6.59 (d, 1H, J=1.96 Hz), 6.32 (dd, 1H, J=2.18, 8.28 Hz), 4.88 (br s, 2H); MS (ESI) 166 (M+1, 100%).

Provenance & Evidence