2-Aminothiazole → 5-Fluoro-2-(2-methylsulfanylphenoxy)-1-nitrobenzene

HRID 1983262Notes

Reaction equation

HRID 1983262 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].F[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]1[CH:23]=[CH:24][C:25]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36][CH3:37])=[C:26]([CH:28]=1)[NH2:27].[NH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH3:9])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1.[F:21][C:22]1[CH:23]=[CH:24][C:25]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36][CH3:37])=[C:26]([NH:27][C:2]([NH:38][C:39]2[S:40][CH:41]=[CH:42][N:43]=2)=[O:1])[CH:28]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 61261o-(Methylthio)phenolHCID 677672,5-DifluoronitrobenzeneHCID 636484715-Fluoro-2-(2-methylsulfanylphenoxy)aniline2×

Product 2

HCID 59732844N-[5-Fluoro-2-(2-methylsulfanylphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 65%HCID 669989725-Fluoro-2-(2-methylsulfanylphenoxy)-1-nitrobenzeneYield 68%

Procedure

5-Fluoro-2-(2-methylsulfanylphenoxy)-1-nitrobenzene (0.95 g, 68%) was prepared from 2-hydroxythioanisole (0.77 g, 5.5 mmol) and 2,5-difluoro-1-nitrobenzene (0.80 g, 5.0 mmol) following the general procedure A. This was reduced to 5-fluoro-2-(2-methylsulfanyl-phenoxy)aniline (0.52 g, 62%) following general procedure B. N-[5-Fluoro-2-(2-methylsulfanylphenoxy)phenyl]-N′-(thiazol-2-yl)urea (120 mg, 65%) was prepared from 5-fluoro-2-(2-methylsulfanylphenoxy)aniline (125 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-8b6c31eebb664b85bdb4efd3876f72ba
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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