4-Fluorophenyl isocyanate → 1-(4-fluorophenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)urea

HRID 62047Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>O1CCCC1>[F:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:19][C:18]2[CH:20]=[CH:21][C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:22])[F:23])=[CH:9][CH:8]=4)[N:11]=3)=[CH:16][CH:17]=2)=[O:33])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline (0.200 g, 0.624 mmol) and 1-fluoro-4-isocyanatobenzene (0.257 g, 1.87 mmol) in a 25 mL round-bottomed flask was added tetrahydrofuran (10 mL). The solution was heated to 65° C. for 2 hours before the solvent was removed under reduced pressure. Purification by flash column chromatography provided the title compound (0.140 g, 49%).

Workup

customwas removed under reduced pressure
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-c2a4e8b722e24e459dc9dfc5cf75c201
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09445594B2

Reaction notes

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