2-Aminothiazole → HCID 19912240, compound

HRID 131826Notes

Reaction equation

HRID 131826 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.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][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[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:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[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][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[C:26]([NH:27][C:6]([NH:38][C:39]2[S:40][CH:41]=[CH:42][N:43]=2)=[O:9])[CH:28]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 90154-MethoxyphenolHCID 677672,5-DifluoronitrobenzeneHCID 19627138HCID 19627138, compound2×

Product 2

HCID 19912240HCID 19912240, compoundYield 80%HCID 59732705HCID 59732705, compoundYield 74%

Procedure

5-Fluoro-2-(4-methoxyphenoxy)-1-nitrobenzene (1.05 g, 80%) was prepared from 4-methoxyphenol (0.68 g, 5.5 mmol) and 2,5-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol) following the general procedure A. This compound was reduced to 5-fluoro-2-(4-methoxyphenoxy)aniline (0.62 g, 66%) following the general procedure B. N-[5-Fluoro-2-(4-methoxyphenoxy)phenyl]-N′-(thiazol-2-yl)urea (133 mg, 74%) was prepared from 2-(4-methoxyphenoxy)-5-fluoroaniline (117 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-49fef6e13b374400946ad622dba61a79
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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