2-Aminothiazole → 2-(2,3-Dimethoxyphenoxy)-6-fluoro-nitrobenzene

HRID 598961Notes

Reaction equation

HRID 598961 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].F[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N+:20]([O-:22])=[O:21].COC1C(OC)=CC=CC=1OC1C=CC=C(F)C=1N.NC1SC=CN=1>COC1C(OC)=CC=CC=1OC1C=CC=C(F)C=1NC(NC1SC=CN=1)=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[O:11][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 788282,3-DimethoxyphenolHCID 879221,3-Difluoro-2-nitrobenzeneHCID 669989052-(2,3-Dimethoxyphenoxy)-6-fluoroaniline2×

Product 1

HCID 669990092-(2,3-Dimethoxyphenoxy)-6-fluoro-nitrobenzeneYield 72%

Reagents, catalysts & solvents 1

HCID 59732837N-[2-(2,3-Dimethoxyphenoxy)-6-fluorophenyl]-N'-(thiazol-2-yl)ureaCatalyst

Procedure

2-(2,3-Dimethoxyphenoxy)-6-fluoro-nitrobenzene (1.05 g, 72%) was prepared from 2,3-dimethoxyphenol (0.85 g, 5.5 mmol) and 2,6-difluoronitrobenzene (0.80 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(2,3-dimethoxyphenoxy)-6-fluoroaniline (0.66 g, 70%) following the general procedure C N-[2-(2,3-Dimethoxyphenoxy)-6-fluorophenyl]-N′-(thiazol-2-yl)urea (136 mg, 70%) was prepared from 2-(2,3-dimethoxyphenoxy)-6-fluoroaniline (131 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-199a1692b2c54f8b92780d894a5faba9
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Reaction notes

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