2-Amino-2-(4-methoxyphenyl)ethan-1-ol → 1-(2-Hydroxy-1-(4-methoxyphenyl)ethyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

HRID 520232Notes

Reaction equation

HRID 520232 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH2:3][OH:4].[N:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]=[CH:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[N:23]=2)=[CH:18][CH:17]=1)=[C:14]=[S:15]>>[OH:4][CH2:3][CH:2]([NH:1][C:14]([NH:13][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]=[CH:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=3)[N:23]=2)=[CH:18][CH:17]=1)=[S:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 136174822-Amino-2-(4-methoxyphenyl)ethan-1-olHCID 1185901713-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1185901371-(2-Hydroxy-1-(4-methoxyphenyl)ethyl)-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-methoxyphenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.42 g, quantitative): 1H NMR (300 MHz, CDCl3) δ 8.06 (s, 1H), 7.66 (d, J=8.3 Hz, 2H), 7.31 (d, J=8.5 Hz, 2H), 7.21 (d, J=8.1 Hz, 3H), 6.76 (d, J=8.3 Hz, 2H), 6.66 (s, 3H), 6.30 (d, J=8.2 Hz, 3H), 5.19-5.01 (m, 1H), 3.50-3.23 (m, 2H), 3.20 (s, 3H); ESIMS m/z 514 ([M+H]+).

Workup

  1. customisolated as a white solid (1.42 g, quantitative)

Sources & evidence

ORD record
ord-ea5f970b397a4dd49f984c00ad0751b6
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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