2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(2,6-Dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole

HRID 1769281Notes

Reaction equation

HRID 1769281 reaction equation
[NH2:1][C:2]([C:20]#[N:21])=[C:3]([N:6]=[CH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[Cl:19])[C:4]#[N:5].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(#N)C>[Cl:14][C:13]1[CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=[C:9]([Cl:19])[C:8]=1[C:7]1[NH:1][C:2]([C:20]#[N:21])=[C:3]([C:4]#[N:5])[N:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 68546627HCID 68546627, compound

Product 1

HCID 189476852-(2,6-Dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazoleYield 42.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-amino-2-(2,6-dichloro-4-trifluoromethylbenzylideneamino)-1,2-dicyanoethylene (3.3 g, 0.01 mol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.3 g, 0.01 mol) in acetonitrile (75 ml) was stirred at reflux for 48 hours. Evaporation of the solvent yielded a brown solid which was continuously extracted with boiling toluene. The solution was evaporated under reduced pressure and the red-brown residue was dissolved in a mixture of ethyl acetate and dichloromethane (1:10) and filtered through silica. Evaporation of the liltrate gave a brown solid which was triturated with hexane and the solid was removed by filtration to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole (1.4 g) as a light brown solid, m.p. 194°-195° C.

Workup

  1. temperatureat reflux for 48 hours
  2. customEvaporation of the solvent
  3. customyielded a brown solid which
  4. extractionwas continuously extracted with boiling toluene
  5. customThe solution was evaporated under reduced pressure
  6. dissolutionthe red-brown residue was dissolved in a mixture of ethyl acetate and dichloromethane (1:10)
  7. filtrationfiltered through silica
  8. customEvaporation of the
  9. customliltrate gave a brown solid which
  10. customwas triturated with hexane
  11. customthe solid was removed by filtration

Sources & evidence

ORD record
ord-fcb3c733f98742ddac413f5e0a32ff0d
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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