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2-Aminothiazole → 1-Nitro-2-[2-(trifluoromethyl)phenoxy]benzene

HRID 559855
Notes
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Reaction equation

HRID 559855 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][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[F:22][C:23]([F:39])([F:38])[C:24]1[CH:37]=[CH:36][CH:35]=[CH:34][C:25]=1[O:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29].[NH2:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1>>[F:11][C:8]([F:9])([F:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[F:22][C:23]([F:38])([F:39])[C:24]1[CH:37]=[CH:36][CH:35]=[CH:34][C:25]=1[O:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][C:2]([NH:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1)=[O:1]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 679582-TrifluoromethylphenolHCID 738951-Fluoro-2-nitrobenzeneHCID 203621012-[2-(Trifluoromethyl)phenoxy]aniline2×

Product 2

HCID 201633111-Nitro-2-[2-(trifluoromethyl)phenoxy]benzeneYield 65%
HCID 59733085
n-[2-(2-Trifluoromethylphenoxy)phenyl]-n'-(thiazol-2-yl)urea
Yield 61%

Procedure

2-[2-(Trifluoromethyl)phenoxy]-1-nitrobenzene (0.92 g, 65%) was prepared from 2-hydroxybenzotrifluoride (0.89 g, 5.5 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This was reduced to 2-[2-(trifluoromethyl)phenoxy]aniline (0.56 g, 68%) following general procedure B. N-[2-(2-Trifluoromethylphenoxy)phenyl]-N′-(thiazol-2-yl)urea (115 mg, 61%) was prepared from 2-[2-(trifluoromethyl)phenoxy]aniline (127 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-c122a6da8db1483d906836fccfc73573
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063081B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes