2-Aminothiazole → N-[4-Fluoro-2-(2-fluoro-6-methoxyphenoxy)phenyl]-N'-(thiazol-2-yl)urea

HRID 598964Notes

Reaction equation

HRID 598964 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[OH:10].F[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([O:30][C:31]2[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:32]=2[F:39])[CH:24]=1.[NH2:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1>>[F:18][C:16]1[CH:17]=[CH:12][C:13]([N+:19]([O-:21])=[O:20])=[C:14]([O:10][C:3]2[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:15]=1.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:3]([NH:40][C:41]2[S:42][CH:43]=[CH:44][N:45]=2)=[O:10])=[C:25]([O:30][C:31]2[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:32]=2[F:39])[CH:24]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 679672,4-DifluoronitrobenzeneHCID 27373672-Fluoro-6-methoxyphenolHCID 669988784-Fluoro-2-(2-fluoro-6-methoxyphenoxy)aniline2×

Product 2

HCID 59732919N-[4-Fluoro-2-(2-fluoro-6-methoxyphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 65%HCID 669987894-Fluoro-2-(2-fluoro-6-methoxyphenoxy)-1-nitrobenzeneYield 65%

Procedure

4-Fluoro-2-(2-fluoro-6-methoxyphenoxy)-1-nitrobenzene (0.91 g, 65%) was prepared from 2-fluoro-6-methoxyphenol (0.78 g, 5.5 mmol) and 2,4-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol) following the general procedure F. This compound was reduced to 4-fluoro-2-(2-fluoro-6-methoxyphenoxy)aniline (0.61 g, 75%) following the general procedure C. N-[4-Fluoro-2-(2-fluoro-6-methoxyphenoxy)phenyl]-N′-(thiazol-2-yl)urea (122 mg, 65%) was prepared from 4-fluoro-2-(2-fluoro-6-methoxyphenoxy)aniline (126 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-4ee5340b16ec4a9b9168996c0e679c04
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Reaction notes

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