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

HRID 1250506
Notes
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Reaction equation

HRID 1250506 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[C:5]([C:20]([OH:22])=O)[CH:4]=1.S(Cl)(Cl)=O.C1C=CC=CC=1.[C:33]1([NH:39][NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)(=O)C.CN(C=O)C>[C:33]1([NH:39][NH:40][C:20]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=3)[N:6]=2)=[O:22])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 241BenzeneHCID 7516PhenylhydrazineHCID 24386Thionyl ChlorideHCID 109030764-Methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid

Product 1

HCID 18326224N-(phenylamino)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. additionby treating the obtained mixture
  2. temperatureunder reflux for about 30 minutes
  3. concentrationThe reaction solution was concentrated
  4. additionmixed with methylene chloride
  5. washwashed with saturated brine
  6. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-391cc0bfd002406fa53d1f2090933f25
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06339045B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes