Ammonia → 1,2-Benzenedicarbonitrile, 4,5-dimethoxy-

HRID 982489Notes

Reaction equation

HRID 982489 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1Br.[Cu](C#N)[C:14]#[N:15].N.[CH3:19][N:20](C)C=O>>[C:14]([C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:19]#[N:20])#[N:15]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 27580334,5-DibromoveratroleHCID 178418260HCID 178418260, compound

Product 1

HCID 108778791,2-Benzenedicarbonitrile, 4,5-dimethoxy-Yield 58%

Procedure

A mixture of 106 g (0.36 mols) of 1.2-dibromo-4.5-dimethoxy-benzene, 98 g (1.06 mols) of copper cyanide and 300 ml of dimethylformamide is brought to reflux for five hours, then the mixture is cooled and is poured into 500 ml of 30% ammonia. The residue is again mixed for 10 minutes, then is filtered and washed with water and dried. The product is extracted by ether for 24 hours by using a Soxhlet device and the solvent is evaporated. Thus, 40 g of 1.2-dicyano-4.5 dimethoxybenzene is obtained in the form of white flakes, which corresponds to a yield of 58%.

Workup

  1. temperatureto reflux for five hours
  2. temperaturethe mixture is cooled
  3. additionThe residue is again mixed for 10 minutes
  4. filtrationis filtered
  5. washwashed with water
  6. customdried
  7. extractionThe product is extracted by ether for 24 hours
  8. customthe solvent is evaporated

Sources & evidence

ORD record
ord-7045764668fb40cd91ab83c6bdb9b885
Source dataset
uspto-grants-1991_02
Patent number
US04996311

Reaction notes

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