Reaction #607412

ord-15f0f9a047aa4421a998f1328cbed052

Reaction equation

NC(CO)c1cccc(Cl)c1
2-amino-2-(3-chlorophenyl)ethanol
FC(F)(F)Oc1ccc(-n2cnc(-c3ccc(N=C=S)cc3)n2)cc1
3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole
OCC(NC(=S)Nc1ccc(-c2ncn(-c3ccc(OC(F)(F)F)cc3)n2)cc1)c1cccc(Cl)c1
title compound
OCC(NC(=S)Nc1ccc(-c2ncn(-c3ccc(OC(F)(F)F)cc3)n2)cc1)c1cccc(Cl)c1
1-(1-(3-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol (Galley, G.; et al., WO 2008092785) and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an white solid (1.44 g, 99%): 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.66-7.53 (m, 3H), 7.25-7.08 (m, 2H), 6.77 (dd, J=8.6, 6.3 Hz, 4H), 6.70-6.61 (m, 4H), 6.58 (dd, J=6.4, 2.2 Hz, 1H), 6.49 (d, J=7.8 Hz, 1H), 5.18-4.95 (m, 1H), 3.43 (dd, J=11.3, 3.9 Hz, 1H), 3.31 (dd, J=11.3, 4.6 Hz, 1H); ESIMS m/z 534 ([M+H]+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09326516B2uspto-grants-2016_05