Reaktion #2438137

Reaktionsgleichung

xylene

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

2-chloroaniline

→

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

Ausbeute 15.9%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heating the reaction mixture
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   FiltrationOne hour later, the reaction mixture was filtered
4. 4
   Sonstigeto remove solid matter
5. 5
   WaschenThe organic layer was washed first with 50 ml of 10% hydrochloric acid
6. 6
   WaschenThe mixture was washed further with water
7. 7
   Trocknenwas then dried over anhydrous sodium sulfate
8. 8
   SonstigeSubsequent to removal of the sodium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off
10. 10
    SonstigeThe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)
11. 11
    Sonstigerecrystallization from acetone

Vorschrift

To 200 ml of xylene were added 6.9 g (0.020 mole) of 1,5-bis(2-chlorophenyl)-2-methyl-1,3,5-pentanetrione, 25.5 g (0.20 mole) of 2-chloroaniline and 20.0 g of Molecular Sieves 5A. After heating the reaction mixture under reflux for 2 hours, the reaction mixture was poured into ice water, followed by addition of 200 ml of chloroform thereto and vigorous stirring of the resultant mixture. One hour later, the reaction mixture was filtered to remove solid matter. The organic layer was washed first with 50 ml of 10% hydrochloric acid and then with 50 ml of a 10% aqueous solution of sodium hydroxide. The mixture was washed further with water and was then dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) and then recrystallization from acetone to give 1.4 g of 1,2,6-tris(2-chlorophenyl)-3-methyl-4(1H)-pyridinone having a melting point of 205°-207° C.

Quelle