Water → Dinitrobenzonitrile

HRID 1076989Notes

Reaction equation

HRID 1076989 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].O.[CH3:15][N:16](C)C=O>>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[C:15]#[N:16])([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 118141-Chloro-2,6-dinitrobenzene

Product 1

HCID 520718Dinitrobenzonitrile

Procedure

1-Chloro-2,6-dinitrobenzene (40.4 grams) is dissolved in anhydrous dimethylformamide (200 ml.). Cuprous cyanide (72 grams) is added and the stirred reaction mixture is heated to reflux for 6 hours. The dark brown reaction mixture is cooled and poured into water (1.5 l.) with stirring. The tan precipitate is collected by filtration and then extracted three times with hot ethanol (300 ml.). Removal of two-thirds of the solvent from combined ethanol extracts under reduced pressure gives a tan precipitate. The precipitate is collected by filtration and recrystallized from ethanol to give a tan product (7.2 grams) melting at 143°-146.5°.

Workup

  1. customthe stirred reaction mixture
  2. temperatureis heated
  3. temperatureto reflux for 6 hours
  4. temperatureThe dark brown reaction mixture is cooled
  5. filtrationThe tan precipitate is collected by filtration
  6. extractionextracted three times with hot ethanol (300 ml.)
  7. customRemoval of two-thirds of the solvent
  8. customgives a tan precipitate
  9. filtrationThe precipitate is collected by filtration
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-05229c5d1af245dbb7bcd6b4df8c323a
Source dataset
uspto-grants-1976_05
Patent number
US03959289

Reaction notes

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