Reacción #1396

Ecuación de reacción

1,10-phenanthroline

bis(3,4-dimethylphenyl)amine

4-iodobiphenyl

potassium hydroxide

→

product

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

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a 500 milliliter round bottomed flask equipped with mechanical stirrer
2. 2
   Otrofitted with a Dean-Stark trap under a reflux condenser
3. 3
   Temperaturamaintained at this temperature for 4 hours after which time chromatographic analysis
4. 4
   Otrothe reaction
5. 5
   TemperaturaThe reaction was cooled to room temperature, about 25° C.
6. 6
   Otropartitioned between 200 milliliters of toluene and 150 milliliters of deionized water
7. 7
   OtroThe resulting organic layer was separated
8. 8
   Otrowater 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
    Lavadoan acid washed clay, and 10 grams of Alcoa CG-20 alumina
11. 11
    Temperaturaat reflux
12. 12
    Filtraciónthe solution was hot filtered
13. 13
    Otroto remove the clay and alumina
14. 14
    Temperaturacooled to room temperature
15. 15
    OtroEvaporation of the solvent and recrystallization from octane

Procedimiento

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.

Fuente