Ammonia → 2,5-Dimethylterephthalonitrile

HRID 855471Notes

Reaction equation

HRID 855471 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5](Br)=[CH:4][C:3]=1[CH3:10].[C:11]([Cu])#[N:12].[CH3:14][N:15](C)C=O.N>O>[CH3:10][C:3]1[CH:4]=[C:5]([C:11]#[N:12])[C:6]([CH3:8])=[CH:7][C:2]=1[C:14]#[N:15]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 66175Benzene, 1,4-dibromo-2,5-dimethyl-HCID 178418546HCID 178418546, compound

Product 1

HCID 6400222,5-DimethylterephthalonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 g of 2,5-Dibromo-p-xylene (0.227 mole), 42.4 g of CuCN (0.568 mole) and 300 ml of dimethylformamide were added into a round-bottom flask, and then the reaction was performed at 130° C. for 12 hours. After completion of the reaction, the reaction mixture was added to the mixing solution of 300 ml of water and 300 ml of aqueous ammonia, and extracted crystal therefrom was filtered. Then, the crystal was added again to the mixing solution of 100 ml of water and 300 ml of aqueous ammonia, mixed and filtered. The obtained crystal was added to 2,000 ml of toluene, heated to dissolve, and treated with active carbon. The filtrate was evaporated in vacuum, and then 300 ml of hexane was added thereto to obtain 20 g of white crystal (0.128 mole, yield: 56%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted crystal
  3. filtrationtherefrom was filtered
  4. additionThen, the crystal was added again to the mixing solution of 100 ml of water and 300 ml of aqueous ammonia
  5. additionmixed
  6. filtrationfiltered
  7. additionThe obtained crystal was added to 2,000 ml of toluene
  8. temperatureheated
  9. dissolutionto dissolve
  10. additiontreated with active carbon
  11. customThe filtrate was evaporated in vacuum
  12. addition300 ml of hexane was added

Sources & evidence

ORD record
ord-beae829bb0074c1b9c7451dcc976c558
Source dataset
uspto-grants-2007_08
Patent number
US07261952B2

Reaction notes

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