2-Aminothiazole → N-[2-(2,6-Dimethoxyphenoxy)phenyl]-N'-(thiazol-2-yl)urea

HRID 559856Notes

Reaction equation

HRID 559856 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[OH:11].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[CH3:22][O:23][C:24]1[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[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>>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:11][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[CH3:39][O:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:24]([O:23][CH3:22])[C:25]=1[O:26][C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH:29][C:4]([NH:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1)=[O:11]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 70412,6-DimethoxyphenolHCID 738951-Fluoro-2-nitrobenzeneHCID 284017052-(2,6-Dimethoxyphenoxy)aniline2×

Product 2

HCID 59733055N-[2-(2,6-Dimethoxyphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 63%HCID 66998647HCID 66998647, compoundYield 63%

Procedure

2-(2,6-Dimethoxyphenoxy)-1-nitrobenzene (0.85 g, 63%) was prepared from 2,6-di-methoxyphenol (0.85 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-(2,6-dimethoxyphenoxy)aniline (0.51 g, 68%) following general procedure C. N-[2-(2,6-Dimethoxyphenoxy)phenyl]-N′-(thiazol-2-yl)-urea (117 g, 63%) was prepared from 2-(2,6-dimethoxyphenoxy)aniline (123 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-29fd3a977cd54e96ac48ca9746daab6a
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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