2-Aminothiazole → 1-(3-Methoxyphenoxy)-2-nitrobenzene

HRID 131801Notes

Reaction equation

HRID 131801 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH2:28].[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][CH:35]=1)[O:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH:28][C:5]([NH:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1)=[O:9]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 90073-MethoxyphenolHCID 738951-Fluoro-2-nitrobenzeneHCID 130002722-(3-Methoxyphenoxy)aniline2×

Product 2

HCID 93111371-(3-Methoxyphenoxy)-2-nitrobenzeneYield 69%HCID 59733009N-[2-(3-Methoxyphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 68%

Procedure

2-(3-Methoxyphenoxy)-1-nitrobenzene (0.84 g, 69%) was prepared from 3-methoxyphenol (0.68 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-(3-methoxyphenoxy)aniline (0.51 g, 70%) following general procedure B. N-[2-(3-Methoxyphenoxy)phenyl]-N′-(thiazol-2-yl)urea (136 mg, 68%) was prepared from 2-(3-methoxyphenoxy)aniline (108 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-b03eafa2ff9c4f3bb88779c5c0cdf89e
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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