Sodium Cyanide → 3-Chlorobenzoyl cyanide

HRID 614029Notes

Reaction equation

HRID 614029 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C-:11]#[N:12].[Na+]>[Cu]C#N>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([C:11]#[N:12])=[O:6]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 69252Benzoyl chloride, 3-chloro-

Product 1

HCID 119842783-Chlorobenzoyl cyanideYield 96.5%

Reagents, catalysts & solvents 1

HCID 178418546HCID 178418546, compoundCatalyst

Conditions

Temperature
220 °C

Procedure

175 g (1 mol) of 3-chlorobenzoyl chloride, 48.5 g (0.97 mol) of sodium cyanide and 2.7 g of copper(I) cyanide were mixed in a three-necked flask and the mixture was warmed to 220° C. in the course of 90 minutes, whilst stirring. the reaction product was removed from the sodium chloride by applying a vacuum. Fractional distillation gave 155 g (94% of theory) of 3-chlorobenzoyl cyanide; boiling point: 112°-115° C. at 12 mm Hg.

Workup

  1. customthe reaction product was removed from the sodium chloride
  2. distillationFractional distillation

Sources & evidence

ORD record
ord-8e8ca282d91440a78b94b7744e1746ec
Source dataset
uspto-grants-1979_03
Patent number
US04143068

Reaction notes

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