4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline → 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole

HRID 520218Notes

Reaction equation

HRID 520218 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][C:18](OC(F)(F)F)=[CH:17][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[F:26][C:27]([F:47])([F:46])C1C=CC(N2C=NC(C3C=CC(N)=CC=3)=N2)=CC=1>>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([C:27]([F:47])([F:46])[F:26])=[CH:19][CH:20]=3)[N:11]=2)=[CH:8][CH:9]=1)=[C:2]=[S:3]

Participants

3

Reactant 2

HCID 893731204-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)anilineHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1185901713-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleYield 94%

Procedure

Prepared according to the procedure reported in (WO 2011017513) for 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole from 4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline and isolated as a white solid (10.6 g, 94%): 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.73-7.41 (m, 2H), 7.41-7.05 (m, 4H), 6.92-6.63 (m, 2H); ESIMS m/z 347 ([M+H]+).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6d3545a3468b41a0802d6c7984b5870c
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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