2-Aminothiazole → 1,2-Difluoro-4-(2-nitrophenoxy)benzene

HRID 1983237Notes

Reaction equation

HRID 1983237 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[F:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[F:35])[O:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[F:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[F:35])[O:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH:27][C:4]([NH:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1)=[O:9]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 738951-Fluoro-2-nitrobenzeneHCID 759273,4-DifluorophenolHCID 43554656HCID 43554656, compound2×

Product 2

HCID 524380751,2-Difluoro-4-(2-nitrophenoxy)benzeneYield 60%HCID 59732788HCID 59732788, compoundYield 60%

Procedure

2-(3,4-Difluorophenoxy)-1-nitrobenzene (0.76 g, 60%) was prepared from 3,4-difluorophenol (0.65 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-(3,4-difluorophenoxy)aniline (0.33 g, 60%, 2.5 mmol scale) following general procedure B. N-[2-(3,4-Difluorophenoxy)phenyl]-N′-(thiazol-2-yl)urea (312 mg, 60%) was prepared from 2-(3,4-difluorophenoxy)aniline (330 mg, 1.5 mmol) and 2-aminothiazole (150 mg, 1.5 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-2ccdc137b5a945c48795abe6c7568963
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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