Sodium Iodide → 2,4-Dichlorobenzoyl Cyanide

HRID 1165988Notes

Reaction equation

HRID 1165988 reaction equation
[I-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7].[C:14](#[N:16])C>>[Cl:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([C:14]#[N:16])=[O:7]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 666452,4-Dichlorobenzoyl chloride

Product 1

HCID 98342322,4-Dichlorobenzoyl Cyanide

Procedure

The reaction was carried out under Argon. Cuprous cyanide (5.0 g, 56.0 mmol) and anhydrous sodium iodide (15.6 g, 104 mmol) were stirred for 2 minutes in anhydrous acetonitrile (100 ml). The resulting solution was mixed with 2,4-dichlorobenzoyl chloride (10.96 g, 52.3 mmol) whereupon an orange precipitate formed. The mixture was stirred for 30 minutes at room temperature, filtered and concentrated in vacuo. The residue was taken up in dichloromethane and the resulting precipitate was filtered off. Concentration of the filtrate under reduce pressure gave a yellow solid which was recrystallised from 60°-80° C. b.p.t. petroleum ether to give 2,4-dichlorobenzoyl cyanide as cream coloured crystals (8.36 g, 80%), melting point 73°-74° C.

Workup

  1. customformed
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. filtrationthe resulting precipitate was filtered off
  5. customgave a yellow solid which
  6. customwas recrystallised from 60°-80° C. b.p.t

Sources & evidence

ORD record
ord-b86afeb512db4795be203265c1090aac
Source dataset
uspto-grants-1990_03
Patent number
US04912262

Reaction notes

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