Reaktion #1396

Reaktionsgleichung

1,10-phenanthroline

bis(3,4-dimethylphenyl)amine

4-iodobiphenyl

potassium hydroxide

→

product

N,N-bis(3,4-dimethylphenyl)-4-biphenylamine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 500 milliliter round bottomed flask equipped with mechanical stirrer
2. 2
   Sonstigefitted with a Dean-Stark trap under a reflux condenser
3. 3
   Temperaturmaintained at this temperature for 4 hours after which time chromatographic analysis
4. 4
   Sonstigethe reaction
5. 5
   TemperaturThe reaction was cooled to room temperature, about 25° C.
6. 6
   Sonstigepartitioned between 200 milliliters of toluene and 150 milliliters of deionized water
7. 7
   SonstigeThe resulting organic layer was separated
8. 8
   Sonstigewater removed by azeotropic distillation of the solvent under a Dean-Stark trap
9. 9
   workup.ADDITIONtreating the toluene solution with 10 grams of Filtrol-24™
10. 10
    Waschenan acid washed clay, and 10 grams of Alcoa CG-20 alumina
11. 11
    Temperaturat reflux
12. 12
    Filtrationthe solution was hot filtered
13. 13
    Sonstigeto remove the clay and alumina
14. 14
    Temperaturcooled to room temperature
15. 15
    SonstigeEvaporation of the solvent and recrystallization from octane

Vorschrift

In a 500 milliliter round bottomed flask equipped with mechanical stirrer and fitted with a Dean-Stark trap under a reflux condenser were placed 12.39 grams (0.055 mole) of bis(3,4-dimethylphenyl)amine, 14 grams (0.050 mole) of 4-iodobiphenyl, 0.25 gram (0.0025 mole) of cuprous chloride, 0.45 gram (0,0025 mole) of 1,10-phenanthroline, 22.44 grams (0.4 mole) of flake potassium hydroxide and 20 milliliters of toluene solvent. The reaction was heated quickly to a reflux temperature of 120° C. and maintained at this temperature for 4 hours after which time chromatographic analysis revealed the reaction to be complete. The reaction was cooled to room temperature, about 25° C., and partitioned between 200 milliliters of toluene and 150 milliliters of deionized water. The resulting organic layer was separated and water removed by azeotropic distillation of the solvent under a Dean-Stark trap. The product was decolorized by slurry treating the toluene solution with 10 grams of Filtrol-24™, an acid washed clay, and 10 grams of Alcoa CG-20 alumina. After 3 hours stirring at reflux, the solution was hot filtered to remove the clay and alumina, and cooled to room temperature. Evaporation of the solvent and recrystallization from octane provided the above product compound in a yield of 10.2 grams (76 percent) and which product melted at 113.8° C. This product of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine was suitable for further purification by conventional means to afford electronic grade, about 99 percent pure, product. The above total reaction time was an accelerated 4 hours.

Quelle