Reaktion #932479

Reaktionsgleichung

5-(2-chlorophenyl)-2-methyl-1-phenyl-1,3,5-pentanetrione

2,6-difluoroaniline

para-toluenesulfonic acid

→

6-(2-chlorophenyl)-1-(2,6-difluorophenyl)-3-methyl-2-phenyl-4(1H)-pyridinone

Ausbeute 24.5%

Lösungsmittel

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby reflux for 8 hours
2. 2
   FiltrationSolid matter was filtered off from the reaction mixture and 300 ml of chloroform
3. 3
   workup.ADDITIONwas added to the filtrate
4. 4
   SonstigeThe mixture obtained
5. 5
   Waschenwas washed first with 50 ml of 10% hydrochloric acid
6. 6
   WaschenAfter washing the chloroform layer further with water, it
7. 7
   Trocknenwas dried over anhydrous sodium sulfate
8. 8
   SonstigeSubsequent to removal of the sodium solfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off
10. 10
    Sonstigeto afford crystals
11. 11
    SonstigeThe crystals were recrystallized from a 2:1 mixed solvent of acetone and hexane

Vorschrift

In 200 ml of xylene were dissolved 6.3 g (0.020 mole) of 5-(2-chlorophenyl)-2-methyl-1-phenyl-1,3,5-pentanetrione, 20.0 g (0.155 mole) of 2,6-difluoroaniline, 4.6 g (0.024 mole) of para-toluenesulfonic acid and 50.0 g of Molecular Sieves 5A, followed by reflux for 8 hours. Solid matter was filtered off from the reaction mixture and 300 ml of chloroform was added to the filtrate. The mixture obtained was washed first with 50 ml of 10% hydrochloric acid and then with 50 ml of a 10% aqueous solution of sodium hydroxide. After washing the chloroform layer further with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium solfate, the solvent was distilled off and the residue was subjected to column chromatography (eluent: ethyl acetate) to afford crystals. The crystals were recrystallized from a 2:1 mixed solvent of acetone and hexane, thereby yielding 2.0 g of 6-(2-chlorophenyl)-1-(2,6-difluorophenyl)-3-methyl-2-phenyl-4(1H)-pyridinone having a melting point of 213°-215° C.

Quelle