Reaction #2484250

Reaction equation

3,4-dimethylacetanilide

4-bromo-o-xylene

potassium hydroxide

potassium carbonate

→

3,3',4,4'-tetramethyldiphenylamine

Yield 70.6%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherIn a 2-liter three-neck flask were placed
2. 2
   Otherthe reaction for 60 hours at 200° C. under a nitrogen gas stream
3. 3
   workup.ADDITIONTo the reaction mixture was added a solution
4. 4
   Otherobtained
5. 5
   Temperaturethe mixture was refluxed for 4 hours
6. 6
   Temperaturethe reaction mixture was cooled to room temperature
7. 7
   Otherinorganic salts were removed by filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off from the filtrate under reduced pressure
9. 9
   OtherThe remaining filtrate was recrystallized from methanol under reduced pressure (about 155° C./0.2 mmHg)

Procedure

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) (2) Synthesis of 3,3',4,4',4"-pentamethyltriphenylamine (CT-13)

Source