2-Aminothiazole → 5-Fluoro-2-(2-trifluromethylphenoxy)-1-nitrobenzene

HRID 131828

Reaction equation

HRID 131828 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].F[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]([F:41])([F:40])[F:39])=[C:28]([CH:30]=1)[NH2:29].[NH2:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]([F:9])([F:10])[F:11])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1.[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]([F:39])([F:40])[F:41])=[C:28]([NH:29][C:2]([NH:42][C:43]2[S:44][CH:45]=[CH:46][N:47]=2)=[O:1])[CH:30]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 677672,5-DifluoronitrobenzeneHCID 679582-TrifluoromethylphenolHCID 284120972-(2-Trifluoromethylphenoxy)-5-fluoroaniline2×

Product 2

HCID 59732964n-[5-Fluoro-2-(2-trifluoromethylphenoxy)phenyl]-n'-(thiazol-2-yl)ureaYield 74%HCID 669989925-Fluoro-2-(2-trifluromethylphenoxy)-1-nitrobenzeneYield 78%

Procedure

5-Fluoro-2-(2-trifluromethylphenoxy)-1-nitrobenzene (1.17 g, 78%) was prepared from 2-hydroxybenzotrifluoride (0.89 g, 5.5 mmol) and 2,5-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol) following the general procedure A. This compound was reduced to 5-fluoro-2-(2-trifluoromethylphenoxy)-aniline (0.65 g, 62%) following the general procedure B. N-[5-Fluoro-2-(2-trifluoromethylphenoxy)phenyl]-N′-(thiazol-2-yl)urea (146 mg, 74%) was prepared from 2-(2-trifluoromethylphenoxy)-5-fluoroaniline (135 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-133e894ea7794596b43a09df1b648e6c
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Linked notes

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