2-Aminothiazole → 2-Nitrotoluene

HRID 1983410Notes

Reaction equation

HRID 1983410 reaction equation
F[C:2]1C=CC=C(OC)[C:3]=1[OH:10].F[C:12]1[CH:13]=[C:14](C)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19].FC1C=CC(N)=C(OC2C(OC)=CC=CC=2F)C=1.[F:40][C:41]1[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[C:42]=1[O:43][C:44]1[CH:50]=[C:49]([CH3:51])[CH:48]=[CH:47][C:45]=1[NH2:46].[NH2:58][C:59]1[S:60][CH:61]=[CH:62][N:63]=1>>[N+:18]([C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:2])([O-:20])=[O:19].[F:40][C:41]1[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[C:42]=1[O:43][C:44]1[CH:50]=[C:49]([CH3:51])[CH:48]=[CH:47][C:45]=1[NH:46][C:3]([NH:58][C:59]1[S:60][CH:61]=[CH:62][N:63]=1)=[O:10]

Participants

7

Reactant 5

HCID 21552-AminothiazoleHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 27373672-Fluoro-6-methoxyphenolHCID 669988784-Fluoro-2-(2-fluoro-6-methoxyphenoxy)anilineHCID 669990022-(2-Fluoro-6-methoxy-phenoxy)-4-methyl-aniline

Product 2

HCID 69442-NitrotolueneYield 65%HCID 597328051-[2-(2-Fluoro-6-methoxy-phenoxy)-4-methyl-phenyl]-3-thiazol-2-yl-ureaYield 65%

Procedure

3-2-fluoro-6-methoxyphenoxy)-nitrotoluene (0.9 g, 65%) was prepared from 2-fluoro-6-methoxyphenol (0.78 g, 5.5 mmol) and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure A. This compound was reduced to 4-fluoro-2-(2-fluoro-6-methoxyphenoxy)aniline (0.58 g, 72%) following the general procedure C. 1-[2-(2-Fluoro-6-methoxy-phenoxy)-4-methyl-phenyl]-3-thiazol-2-yl-urea (122 mg, 65%) was prepared from 2-(2-fluoro-6-methoxy-phenoxy)-4-methyl-aniline (124 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-4f60817d0f64489fa305b140a972d0a0
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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