2H-Imidazole, 2,2,4,5-tetrachloro- → HCID 12278431, compound

HRID 1973408Notes

Reaction equation

HRID 1973408 reaction equation
[Cl:1][C:2]1([Cl:9])[N:6]=[C:5](Cl)[C:4]([Cl:8])=[N:3]1.[Cu][C:11]#[N:12]>C1(C)C(C)=CC=CC=1>[C:11]([C:5]1[C:4]([Cl:8])=[N:3][C:2]([Cl:1])([Cl:9])[N:6]=1)#[N:12]

Participants

4

Reactant 2

HCID 122783972H-Imidazole, 2,2,4,5-tetrachloro-HCID 178418546HCID 178418546, compound

Product 1

HCID 12278431HCID 12278431, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 20.5 g (0.1 mol) of 2,2,4,5-tetrachloro-2H-imidazole, 41 g (0.5 mol) of anhydrous copper-(I) cyanide and 230 ml of anhydrous xylene was heated for about 30 hours at 110° - 120° C. After cooling, the reaction mixture was filtered and the brown residue was repeatedly washed with ether. The combined solutions were shaken with active charcoal and the resulting coloured solution was concentrated in vacuo. The concentrated solution was taken up in n-hexane and the product crystallised out. It was filtered off and recrystallised from n-hexane, giving 7.9 g (40% of theory) of 4-cyano-2,2,5-trichloroimidazole (melting point 114° - 115° C).

Workup

  1. temperaturewas heated for about 30 hours at 110° - 120° C
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. washthe brown residue was repeatedly washed with ether
  5. concentrationthe resulting coloured solution was concentrated in vacuo
  6. customthe product crystallised out
  7. filtrationIt was filtered off
  8. customrecrystallised from n-hexane

Sources & evidence

ORD record
ord-fb7549e84a4649d9a78770c2ebeca11e
Source dataset
uspto-grants-1976_12
Patent number
US03997552

Reaction notes

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