2-Amino-2-(4-methoxyphenyl)ethan-1-ol → 1-(2-hydroxy-1-(4-methoxyphenyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

Participants

Reaction Steps

To 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole (1.09 g, 2.70 mmol) in tetrahydrofuran (7 mL) was added 2-amino-2-(4-methoxyphenyl)ethanol (0.506 g, 3.30 mmol) (Reggelin, M. et al., Synlett, 2012, 23, 1095-1098). The reaction was stirred overnight at room temperature. The reaction mixture was concentrated and the residue was recrystallized with petroleum ether providing the title compound as a white solid (1.42 g, 81%): 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.72-7.57 (m, 2H), 7.27 (s, 1H), 7.23-7.14 (m, 2H), 6.87-6.72 (m, 4H), 6.64-6.56 (m, 2H), 6.38-6.22 (m, 3H), 5.05 (s, 1H), 3.47-3.28 (m, 2H), 3.20 (s, 3H); ESIMS m/z 530 ([M+H]+).

Provenance & Evidence