Ethanolamine → 2-[(2-{2-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]phenoxy}ethyl)amino]ethanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[2-(2-bromoethoxy)phenyl]-2-(trifluoromethyl)-1,3-thiazole (C5) (115 mg, 0.327 mmol) and 2-aminoethanol (0.197 mL, 3.26 mmol) was heated to 80° C. for 3 hours. After cooling to room temperature, the reaction was diluted with dichloromethane and washed with 0.5 N aqueous sodium hydroxide solution, then with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo, yielding the title compound as a white solid. Yield: 113 mg, quantitative. 1H NMR (400 MHz, CDCl3) δ 2.88 (dd, J=5.2, 5.1 Hz, 2H), 3.15 (dd, J=5, 5 Hz, 2H), 3.68 (br dd, J=5, 5 Hz, 2H), 4.25 (dd, J=5, 5 Hz, 2H), 7.03 (br d, J=8.3 Hz, 1H), 7.08-7.12 (m, 1H), 7.33-7.38 (m, 1H), 8.18 (s, 1H), 8.21 (br d, J=7.9 Hz, 1H).

Provenance & Evidence