Potassium Carbonate → Bis(3,4-dimethylphenyl)amine

HRID 1081551

Reaktionsgleichung

Reaktionsgleichung von HRID 1081551
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:11])=O)=[CH:4][C:3]=1[CH3:12].Br[C:14]1[CH:15]=[C:16]([CH3:21])[C:17](C)=[CH:18]C=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>C(O)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:15][C:16]([CH3:21])=[C:17]([CH3:18])[CH:11]=2)=[CH:4][C:3]=1[CH3:12]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 685044-Bromo-o-xyleneHCID 751443',4'-Dimethylacetanilide

Produkt 1

HCID 614511Bis(3,4-dimethylphenyl)amineAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In a 2-liter three-neck flask were placed 120 g of 3,4-dimethylacetanilide synthesized in Example 1 (1), 253 g of unpurified 4-bromo-o-xylene (purity about 70%, containing about 30% 3-bromo-o-xylene), 122 g of anhydrous potassium carbonate and 2 g of copper sulfate pentahydrate, and after carrying out the reaction for 60 hours at 200° C. under a nitrogen gas stream, the reaction mixture was cooled to room temperature. To the reaction mixture was added a solution obtained by dissolving 120 g of potassium hydroxide in 600 ml of ethanol, and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then, inorganic salts were removed by filtration, and the solvent was distilled off from the filtrate under reduced pressure. The remaining filtrate was recrystallized from methanol under reduced pressure (about 155° C/0.2 mmHg) to provide 117 g of 3,3',4,4'-tetramethyldiphenylamine. (Melting point 80° to 82° C., colorless crystals)

Aufarbeitung

  1. customIn a 2-liter three-neck flask were placed
  2. customthe reaction for 60 hours at 200° C. under a nitrogen gas stream
  3. additionTo the reaction mixture was added a solution
  4. customobtained
  5. temperaturethe mixture was refluxed for 4 hours
  6. temperaturethe reaction mixture was cooled to room temperature
  7. custominorganic salts were removed by filtration
  8. distillationthe solvent was distilled off from the filtrate under reduced pressure
  9. customThe remaining filtrate was recrystallized from methanol under reduced pressure (about 155° C/0.2 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-3ab5acca52e847659705dfe91af6056c
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587263

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