2-Amino-2-(4-methylphenyl)ethanol → 1-(2-Hydroxy-1-(p-tolyl)ethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

HRID 520222Notes

Reaction equation

HRID 520222 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[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]>>[OH:4][CH2:3][CH:2]([NH:1][C:13]([NH:12][C:15]1[CH:16]=[CH:17][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:34])[F:35])=[CH:28][CH:27]=3)[N:22]=2)=[CH:19][CH:20]=1)=[S:14])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 113095992-Amino-2-(4-methylphenyl)ethanolHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1185901701-(2-Hydroxy-1-(p-tolyl)ethyl)-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-(p-tolyl)ethanol and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an off-white solid (0.300 g, 71%): mp 145-156° C.; 1H NMR (400 MHz, CD3OD) δ 9.13 (s, 1H), 8.12 (d, J=6.8 Hz, 2H), 8.05 (d, J=2.2 Hz, 2H), 7.65 (d, J=7.4 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 7.24-7.23 (m, 2H), 7.18-7.16 (m, 2H), 5.60 (s, 1H), 3.90-3.84 (m, 2H), 2.34 (s, 3H) (NH, OH not observed); ESIMS m/z 514 ([M+H]+).

Sources & evidence

ORD record
ord-3e35b25db0c04d299f272a3438595ea3
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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