2-Amino-2-(4-chlorophenyl)ethan-1-ol → 1-(1-(4-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

HRID 520221Notes

Reaction equation

HRID 520221 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[CH2:3][OH:4].[N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[N:22]=2)=[CH:17][CH:16]=1)=[C:13]=[S:14]>>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH:2]([NH:1][C:13]([NH:12][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=4)[N:22]=3)=[CH:19][CH:20]=2)=[S:14])[CH2:3][OH:4])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 148531952-Amino-2-(4-chlorophenyl)ethan-1-olHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1185901891-(1-(4-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

Procedure

The title compound was prepared with 2-amino-2-(4-chlorophenyl)ethanol (Chen, L.; et al., US 20060004045) and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an off-white solid (0.300 g, 68%): mp 94-97° C.; 1H NMR (300 MHz, CD3OD) δ 9.12 (s, 1H), 8.11 (d, J=6.8 Hz, 2H), 8.01 (d, J=6.9 Hz, 2H), 7.61 (d, J=8.6 Hz, 2H), 7.49 (d, J=8.3 Hz, 3H), 7.32-7.38 (m, 3H), 5.59 (s, 1H), 3.84-3.87 (m, 2H) (NH, OH not observed); ESIMS m/z 534 ([M+H]+).

Sources & evidence

ORD record
ord-4505cc92bd59464f9829b72ce6bc30b5
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

Loading…