Dimethylformamide → 1,4-Benzenediacetonitrile

HRID 1605210Notes

Reaction equation

HRID 1605210 reaction equation
[C-:1]#[N:2].[Na+].[C:4]1([CH2:12]Cl)[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][CH:5]=1.C[N:15]([CH3:18])C=O>O>[C:4]1([CH2:12][C:18]#[N:15])[CH:9]=[CH:8][C:7]([CH2:10][C:1]#[N:2])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 12171alpha,alpha'-Dichloro-p-xylene2×

Product 1

HCID 693271,4-BenzenediacetonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 130 grams (2.65 moles) sodium cyanide in 200 ml of water was placed in a four-necked flask, equipped with a thermowell, mechanical stirrer, electrically heated addition funnel and a condenser. A solution of 200 grams (1.15 mole) of p-xylylene chloride in 200 ml of dimethyl formamide was added dropwise with constant stirring and such a rate as to maintain the reaction temperature at 60°-65°C. The p-xylylene chloride solution was maintained at about 60°C. to prevent solid precipitation. The reaction was exothermic and addition took 2 hours. At the completion of the addition, the temperature was maintained by external heating for an additional hour. The mixture was then poured into 2 liters of water. The precipitated solid was filtered and washed with an additional liter of water. The product yield was 85% (ca. 152 g.) of para-phenylene diacetonitrile having a melting point of about 95°-97°C.

Workup

  1. customequipped with a thermowell, mechanical stirrer
  2. additionelectrically heated addition funnel and a condenser
  3. temperaturesuch a rate as to maintain the reaction temperature at 60°-65°C
  4. customsolid precipitation
  5. additionaddition
  6. additionAt the completion of the addition
  7. temperaturethe temperature was maintained
  8. temperatureby external heating for an additional hour
  9. additionThe mixture was then poured into 2 liters of water
  10. filtrationThe precipitated solid was filtered
  11. washwashed with an additional liter of water

Sources & evidence

ORD record
ord-ab1663b82830454b9b332e0918257eb7
Source dataset
uspto-grants-1976_04
Patent number
US03950310

Reaction notes

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