Sodium Hydroxide → 4-(Methylthio)-2-(3-(trifluoromethyl)phenyl)-6-(4-(trifluoromethyl)phenyl)pyridine

HRID 231733

Reaction equation

HRID 231733 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[CH3:20][S:21][C:22](SC)=[CH:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)=O.C([O-])(=O)C.[NH4+:42].[OH-].[Na+]>C(O)(=O)C.O1CCCC1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:22]([S:21][CH3:20])[CH:23]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)[N:42]=2)[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 676823'-(Trifluoromethyl)acetophenoneHCID 517165Ammonium AcetateHCID 145512063,3-Bis(methylsulfanyl)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 1894114-(Methylthio)-2-(3-(trifluoromethyl)phenyl)-6-(4-(trifluoromethyl)phenyl)pyridineYield 99.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 20 ml of tetrahydrofuran solution containing 0.64 g of m-trifluoromethylacetophenone was added 0.9 g of potassium t-butoxide at room temperature, followed by stirring for 30 minutes. Further, 1 g of 3,3-bis-(methylthio)-1-(4'-trifluoromethylphenyl)-2-propen-1-one was added, followed by stirring for 1 hour. Subsequently, 20 ml of acetic acid and 3 g of ammonium acetate were added, and reaction was carried out for 3 hours under reflux, while distilling away tetrahydrofuran. The reaction liquid was neutralized with an aqueous solution of sodium hydroxide, and the neutralized solution was extracted twice with 50 ml portion of ethyl acetate. The extract was dried with anhydrous magnesium sulfate. Ethyl acetate was distilled away under reduced pressure and the residues were recrystallized from isopropanol to give 1.4 g of 2-(3'-trifluoromethylphenyl)-4-methylthio-6-(4'-trifluoromethylphenyl)pyridine. (m.p. 98.5° C.)

Workup

  1. stirringby stirring for 1 hour
  2. customreaction
  3. waitwas carried out for 3 hours
  4. temperatureunder reflux
  5. distillationwhile distilling away tetrahydrofuran
  6. customThe reaction liquid
  7. extractionthe neutralized solution was extracted twice with 50 ml portion of ethyl acetate
  8. dry with materialThe extract was dried with anhydrous magnesium sulfate
  9. distillationEthyl acetate was distilled away under reduced pressure
  10. customthe residues were recrystallized from isopropanol

Sources & evidence

ORD record
ord-aad2e82f5c7d4beaa8c357b3e6ebd071
Source dataset
uspto-grants-1989_07
Patent number
US04849011

Linked notes

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