beta-Amino-3-chlorobenzeneethanol → 1-(1-(3-Chlorophenyl)-2-hydroxyethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

HRID 520240Notes

Reaction equation

HRID 520240 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[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:7]1[CH:6]=[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:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 10953980beta-Amino-3-chlorobenzeneethanolHCID 1185901713-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1185901661-(1-(3-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-(3-chlorophenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.48 g, quantitative): 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.69 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.7 Hz, 3H), 7.21 (d, J=8.5 Hz, 2H), 6.83-6.72 (m, 3H), 6.67 (d, J=7.3 Hz, 4H), 6.39 (d, J=7.9 Hz, 1H), 5.09 (s, 1H), 3.14 (dd, J=10.7, 4.4 Hz, 1H), 2.93 (dd, J=10.7, 8.0 Hz, 1H); ESIMS m/z 518 ([M+H]+).

Workup

  1. customisolated as a white solid (1.48 g, quantitative)

Sources & evidence

ORD record
ord-1021f44bd44c48898866cb778987293b
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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