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

HRID 520236Notes

Reaction equation

HRID 520236 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]([C:32]([F:35])([F:34])[F:33])=[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:20]=[CH:19][C:18]([C:21]3[N:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][CH:27]=4)[N:22]=3)=[CH:17][CH:16]=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 1185901713-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1185901571-(1-(4-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

Procedure

The title compound was prepared with 2-amino-2-(4-chlorophenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.4 g, 97%): 1H NMR (300 MHz, CDCl3) δ 8.06 (s, 1H), 7.67 (d, J=8.5 Hz, 2H), 7.31 (d, J=8.7 Hz, 2H), 7.21 (d, J=7.7 Hz, 2H), 6.81-6.51 (m, 8H), 6.41 (s, 1H), 5.70-5.44 (m, 1H), 3.20-2.82 (m, 2H); ESIMS m/z 518 ([M+H]+).

Sources & evidence

ORD record
ord-a5d316c9d42f4cf69e6663e0e450babe
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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