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

HRID 131799Notes

Reaction equation

HRID 131799 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]1[CH:35]=[CH:34][C:25]([O:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH2:29])=[C:24]([O:36][CH3:37])[CH:23]=1.[NH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])=[C:4]([O:9][CH3:10])[CH:3]=1.[F:21][C:22]1[CH:35]=[CH:34][C:25]([O:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH:29][C:10]([NH:38][C:39]2[S:40][CH:41]=[CH:42][N:43]=2)=[O:9])=[C:24]([O:36][CH3:37])[CH:23]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 738951-Fluoro-2-nitrobenzeneHCID 27373684-Fluoro-2-methoxyphenolHCID 597837992-(4-Fluoro-2-methoxyphenoxy)aniline2×

Product 2

HCID 59732715N-[2-(4-Fluoro-2-methoxyphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 71%HCID 597837514-Fluoro-2-methoxy-1-(2-nitrophenoxy)benzeneYield 67%

Procedure

2-(4-Fluoro-2-methoxyphenoxy)-1-nitrobenzene (0.88 g, 67%) was prepared from 4-fluoro-2-methoxyphenol (0.78 g, 5.5 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(4-fluoro-2-methoxyphenoxy)aniline (0.60 g, 78%) following general procedure C. N-[2-(4-Fluoro-2-methoxyphenoxy)phenyl]-N′-(thiazol-2-yl)urea (127 mg, 71%) was prepared from 2-(4-fluoro-2-methoxyphenoxy)aniline (116 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-5ec19eace16749e7b484033ac9e6fd76
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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