2-Aminothiazole → N-[2-(2,3-Dimethoxyphenoxy)-5-methoxyphenyl]-N'-(thiazol-2-yl)urea

HRID 131836

Reaction equation

HRID 131836 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].Cl[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:27]=1[O:28][C:29]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:30]=1[NH2:31].[NH2:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1>>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[O:11][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[C:41]([O:42][CH3:43])=[CH:40][CH:39]=[CH:38][C:27]=1[O:28][C:29]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:30]=1[NH:31][C:4]([NH:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1)=[O:11]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 251404-Chloro-3-nitroanisoleHCID 788282,3-DimethoxyphenolHCID 669987222-(2,3-Dimethoxyphenoxy)-5-methoxyaniline2×

Product 2

HCID 59732942N-[2-(2,3-Dimethoxyphenoxy)-5-methoxyphenyl]-N'-(thiazol-2-yl)ureaYield 62%HCID 669989612-(2,3-Dimethoxyphenoxy)-5-methoxy-1-nitrobenzeneYield 56%

Procedure

2-(2,3-Dimethoxyphenoxy)-5-methoxy-1-nitrobenzene (0.85 g, 56%) was prepared from 2,3-dimethoxyphenol (0.85 g, 5.5 mmol) and 4-chloro-3-nitroanisole (0.94 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2,3-dimethoxyphenoxy)-5-methoxyaniline (0.65 g, 85%) following general procedure C. N-[2-(2,3-Dimethoxyphenoxy)-5-methoxyphenyl]-N′-(thiazol-2-yl)urea (124 g, 62%) was prepared from 2-(2,3-dimethoxyphenoxy)-5-methoxyaniline (133 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-ecb097a327b3416588f028864be2c89e
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Linked notes

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