2-Aminothiazole → 2-(2,4,6-Trifluorophenoxy)-1-nitrobenzene

HRID 598948Notes

Reaction equation

HRID 598948 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]1[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[C:23]=1[O:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].[NH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[O:10][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]1[CH:35]=[C:34]([F:36])[CH:33]=[C:32]([F:37])[C:23]=1[O:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH:27][C:3]([NH:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1)=[O:10]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 738951-Fluoro-2-nitrobenzeneHCID 5199742,4,6-TrifluorophenolHCID 669986132-(2,4,6-Trifluorophenoxy)aniline2×

Product 2

HCID 59732712N-[2-(2,4,6-Trifluorophenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 60%HCID 669989732-(2,4,6-Trifluorophenoxy)-1-nitrobenzeneYield 85%

Procedure

2-(2,4,6-Trifluorophenoxy)-1-nitrobenzene (1.14 g, 85%) was prepared from 2,4,6-trifluorophenol (0.74 g, 5.0 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2,4,6-trifluorophenoxy)aniline (0.42 g, 70%, 2.5 mmol scale) following general procedure B. N-[2-(2,4,6-Trifluorophenoxy)phenyl]-N′-(thiazol-2-yl)urea (219 mg, 60%) was prepared from 2-(2,4,6-trifluorophenoxy)aniline (237 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-45ee6cf501784a7abf7ddef285ea813b
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Reaction notes

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