2-Amino-2-phenylethan-1-ol → (S)-1-(2-Hydroxy-1-phenylethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

HRID 520224Notes

Reaction equation

HRID 520224 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[N:21]=2)=[CH:16][CH:15]=1)=[C:12]=[S:13]>>[OH:4][CH2:3][C@@H:2]([NH:1][C:12]([NH:11][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:33])[F:34])=[CH:27][CH:26]=3)[N:21]=2)=[CH:18][CH:19]=1)=[S:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 1347972-Amino-2-phenylethan-1-olHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 118590173(S)-1-(2-Hydroxy-1-phenylethyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

Procedure

The title compound was prepared with (S)-2-amino-2-phenylethanol and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an off-white solid (0.300 g, 73%): mp 125-128° C.; 1H NMR (400 MHz, CD3OD) δ 9.14 (s, 1H), 8.13 (d, J=8.3 Hz, 2H), 8.04 (d, J=8.8 Hz, 2H), 7.64 (d, J=8.3 Hz, 2H), 7.51 (d, J=8.7 Hz, 2H), 7.43-7.35 (m, 4H), 7.30-7.27 (m, 1H), 5.64 (s, 1H), 3.94-3.86 (m, 2H) (NH, OH not observed); ESIMS m/z 500 ([M+H]+).

Sources & evidence

ORD record
ord-21f33c4d851b440787af007bd0f9a58f
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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