2-Aminothiazole → 3-(2,3-Dimethoxyphenoxy)-4-nitrotoluene

HRID 559885Notes

Reaction equation

HRID 559885 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].F[C:13]1[CH:14]=[C:15]([CH3:22])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20].[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[CH:34]=[C:33]([CH3:35])[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[CH:14]=[C:15]([CH3:22])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20].[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[CH:34]=[C:33]([CH3:35])[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 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 788282,3-DimethoxyphenolHCID 669988362-(2,3-Dimethoxyphenoxy)-4-methylaniline2×

Product 2

HCID 59733062N-[2-(2,3-Dimethoxyphenoxy)-4-methylphenyl]-N'-(thiazol-2-yl)ureaYield 63%HCID 669989243-(2,3-Dimethoxyphenoxy)-4-nitrotolueneYield 64%

Procedure

3-(2,3-Dimethoxyphenoxy)-4-nitrotoluene (0.92 g, 64%) was prepared from 2,3-di-methoxyphenol (0.85 g, 5.5 mmol) and 3-fluoro-4-nitrotoluene (0.78 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2,3-dimethoxyphenoxy)-4-methylaniline (0.65 g, 79%) following general procedure C. N-[2-(2,3-Dimethoxyphenoxy)-4-methylphenyl]-N′-(thiazol-2-yl)urea (120 mg, 63%) was prepared from 2-(2,3-dimethoxyphenoxy)-4-methylaniline (130 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-f138fad02284488d9f7e7cf1d9fc0f9e
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

Loading…