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

HRID 598970

Reaction equation

HRID 598970 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[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:22].[CH3:23][O:24][C:25]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:26]=1[O:27][C:28]1[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:29]=1[NH2:30].[NH2:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=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[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:22].[CH3:23][O:24][C:25]1[C:39]([O:40][CH3:41])=[CH:38][CH:37]=[CH:36][C:26]=1[O:27][C:28]1[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:29]=1[NH:30][C:4]([NH:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1)=[O:11]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 775912-Chloro-3-nitrotolueneHCID 788282,3-DimethoxyphenolHCID 669990242-(2,3-Dimethoxyphenoxy)-3-methylaniline2×

Product 2

HCID 59732737N-[2-(2,3-Dimethoxyphenoxy)-3-methylphenyl]-N'-(thiazol-2-yl)ureaYield 61%HCID 669989282-(2,3-Dimethoxyphenoxy)-3-nitrotolueneYield 56%

Procedure

2-(2,3-Dimethoxyphenoxy)-3-nitrotoluene (0.80 g, 56%) was prepared from 2,3-dimethoxyphenol (0.85 g, 5.5 mmol) and 2-chloro-3-nitrotoluene (0.85 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2,3-dimethoxyphenoxy)-3-methylaniline (0.54 g, 76%) following general procedure C. N-[2-(2,3-Dimethoxyphenoxy)-3-methylphenyl]-N′-(thiazol-2-yl)urea (116 mg, 61%) was prepared from 2-(2,3-dimethoxyphenoxy)-3-methylaniline (130 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-545cb5531dea458bbe0e2319ebd36007
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Linked notes

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