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2-Aminothiazole → 1-(4-Fluorophenoxy)-2-nitrobenzene

HRID 2276089
Notes
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Reaction equation

HRID 2276089 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].[F:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[NH2:27])=[CH:22][CH:21]=1.[NH2:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1.[F:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[NH:27][C:5]([NH:34][C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[O:8])=[CH:22][CH:21]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 97324-FluorophenolHCID 738951-Fluoro-2-nitrobenzeneHCID 64853992-(4-Fluorophenoxy)aniline2×

Product 2

HCID 9611271-(4-Fluorophenoxy)-2-nitrobenzeneYield 75%HCID 59732937
N-[2-(4-Fluorophenoxy)phenyl]-N'-(thiazol-2-yl)urea
Yield 72%

Procedure

2-(4-Fluorophenoxy)-1-nitrobenzene (0.87 g, 75%) was prepared from 4-fluoro-phenol (0.62 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-(4-fluorophenoxy)aniline (0.51 g, 68%) following general procedure B. N-[2-(4-Fluorophenoxy)phenyl]-N′-(thiazol-2-yl)urea (118 mg, 72%) was prepared from 2-(4-fluorophenoxy)aniline (102 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-83bb9bbc59a14634a7e8146b52eb03ba
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE045670E1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes