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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1250506Generated: November 2, 2026

Benzene → N-(phenylamino)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

https://huagongshe.com/reaction/1250506

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzeneHCID 241—
ReactantPhenylhydrazineHCID 7516—
ReactantThionyl ChlorideHCID 24386—
Reactant4-Methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acidHCID 10903076—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductN-(phenylamino)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamideHCID 18326224—

Reaction Steps

0.4 g (0.00128 mol) of 4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxylic acid was mixed with 0.3 g (0.00128×2.0 mol) of thionyl chloride and then with about 10 ml of benzene and a small amount of DMF, followed by treating the obtained mixture under reflux for about 30 minutes. The reaction solution was concentrated and mixed with methylene chloride and then with 0.34 g (0.00128×2.5 mol) of phenyl hydrazine, followed by stirring at room temperature for about one hour. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, and washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06339045B1
Source datasetuspto-grants-2002_01
ORD IDord-391cc0bfd002406fa53d1f2090933f25
Source noteuspto-grants-2002_01