Ethanol → N5-Thiazol-2-yl-benzothiazole-2,5-diamine

Participants

Reaction Steps

To a solution of ethanol (12 mL) was added the urea compound (Example 18, 50 mg, 0.22 mmol) along with chloroacetyaldehyde (0.12 mL, 0.94 mmol). The resulting mixture was heated at reflux for 24 hours. The mixture was then cooled to room temperature and the solvent was evaporated. Water (25 mL) was added to the residue and the pH was adjusted to 9 using sodium carbonate solution. The mixture was extracted using ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated (18.8 mg, 33%).%). 1H-NMR (CDCl3) δ: 7.66 (d, 1H, J=2.2 Hz), 7.47 (d, 1H, J=8.54), 7.21–7.18 (m, 2H), 6.73 (d, 1H, J=3.9 Hz); MS (ESI) 248.8 (M+1, 100%).

Provenance & Evidence