Hydrogen Cyanide → p-Trichloromethylbenzoyl cyanide

HRID 1758014Notes

Reaction equation

HRID 1758014 reaction equation
[CH:1]#[N:2].[Cl:3][C:4]([Cl:15])([Cl:14])[C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1.[C-]#N.[K+]>C(Cl)Cl.O.CN(C)CC1C=CC=CC=1>[Cl:3][C:4]([Cl:15])([Cl:14])[C:5]1[CH:13]=[CH:12][C:8]([C:9]([C:1]#[N:2])=[O:10])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 768Hydrogen CyanideHCID 9032Potassium CyanideHCID 846604-(Trichloromethyl)benzoyl chloride

Product 1

HCID 20510484p-Trichloromethylbenzoyl cyanideYield 48%

Reagents, catalysts & solvents 3

HCID 7681N,N-DimethylbenzylamineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

50 ml of hydrogen cyanide, dissolved in 150 ml of methylene chloride, are added dropwise at -10° C. to -20° C. to a solution of 275 g of p-trichloromethylbenzoyl chloride and 2 g of dimethylbenzylamine in 1.5 l of methylene chloride. Subsequently, a solution of 60 g of potassium cyanide in 120 ml of water is slowly added dropwise at the same temperature and, finally, the mixture is stirred for a further two hours. The solids which have precipitated are filtered off with suction, the phases are separated and the organic phase is washed several times with water, dried over Na2SO4 and concentrated. A little ether is added to the remaining oily residue, whereupon 52 g (20%) of dimeric p-trichloromethylbenzoyl cyanide crystallize out, and the crystals are filtered off with suction. 127 g (48% of theoretical) of p-trichloromethylbenzoyl cyanide can be obtained from the filtrate by vacuum distillation.

Workup

  1. customThe solids which have precipitated
  2. filtrationare filtered off with suction
  3. customthe phases are separated
  4. washthe organic phase is washed several times with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. additionA little ether is added to the remaining oily residue, whereupon 52 g (20%) of dimeric p-trichloromethylbenzoyl cyanide
  8. customcrystallize out
  9. filtrationthe crystals are filtered off with suction

Sources & evidence

ORD record
ord-d5bbc27166774f4f81f51b4aaf702dfe
Source dataset
uspto-grants-1983_02
Patent number
US04371607

Reaction notes

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