2-Aminothiazole → 4,5-Dichloro-2-(2,3-dimethoxyphenoxy)-1-nitrobenzene

HRID 559888

Reaction equation

HRID 559888 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:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[C:15](F)[CH:14]=1.[Cl:24][C:25]1[C:31]([Cl:32])=[CH:30][C:28]([NH2:29])=[C:27]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[C:35]=2[O:42][CH3:43])[CH:26]=1.[NH2:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1>>[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[C:15]([O:11][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=2[O:2][CH3:1])[CH:14]=1.[Cl:24][C:25]1[C:31]([Cl:32])=[CH:30][C:28]([NH:29][C:4]([NH:44][C:45]2[S:46][CH:47]=[CH:48][N:49]=2)=[O:11])=[C:27]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[C:35]=2[O:42][CH3:43])[CH:26]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 788282,3-DimethoxyphenolHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzeneHCID 669989264,5-Dichloro-2-(2,3-dimethoxyphenoxy)aniline2×

Product 2

HCID 59732851N-[4,5-Dichloro-2-(2,3-dimethoxyphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 62%HCID 669990204,5-Dichloro-2-(2,3-dimethoxyphenoxy)-1-nitrobenzeneYield 65%

Procedure

4,5-Dichloro-2-(2,3-dimethoxyphenoxy)-1-nitrobenzene (1.12 g, 65%) was prepared from 2,3-dimethoxyphenol (0.85 g, 5.5 mmol) and 4,5-dichloro-2-fluoro-1-nitrobenzene (1.05 g, 5.0 mmol) following the general procedure A. This was reduced to 4,5-dichloro-2-(2,3-dimethoxyphenoxy)aniline (0.68 g, 67%) following general procedure B. N-[4,5-Dichloro-2-(2,3-dimethoxyphenoxy)phenyl]-N′-(thiazol-2-yl)urea (136 mg, 62%) was prepared from 4,5-dichloro-2-(2,3-dimethoxyphenoxy)aniline (157 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-edee006339014cad809e5ad870f30ec5
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Linked notes

Loading…