반응 #1396

반응 방정식

1,10-phenanthroline

bis(3,4-dimethylphenyl)amine

4-iodobiphenyl

potassium hydroxide

→

product

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

용매

toluene

반응 조건

후처리

1. 1
   기타In a 500 milliliter round bottomed flask equipped with mechanical stirrer
2. 2
   기타fitted with a Dean-Stark trap under a reflux condenser
3. 3
   온도maintained at this temperature for 4 hours after which time chromatographic analysis
4. 4
   기타the reaction
5. 5
   온도The reaction was cooled to room temperature, about 25° C.
6. 6
   기타partitioned between 200 milliliters of toluene and 150 milliliters of deionized water
7. 7
   기타The resulting organic layer was separated
8. 8
   기타water 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
    세척an acid washed clay, and 10 grams of Alcoa CG-20 alumina
11. 11
    온도at reflux
12. 12
    여과the solution was hot filtered
13. 13
    기타to remove the clay and alumina
14. 14
    온도cooled to room temperature
15. 15
    기타Evaporation of the solvent and recrystallization from octane

실험 절차

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.

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