Imidazole → Diphenyl-4,5,6-trichloropyrimid-2-yl-imidazol-1-yl-methane

HRID 1580847Notes

Reaction equation

HRID 1580847 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:9]2[N:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[C:11]([Cl:17])[N:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>C(#N)C>[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:9]2[N:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[C:11]([Cl:17])[N:10]=2)[N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 21393784HCID 21393784, compound

Product 1

HCID 21393786Diphenyl-4,5,6-trichloropyrimid-2-yl-imidazol-1-yl-methane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

34.0 g (0.1 mol) of diphenyl-4,5,6-trichloropyrimid-2-yl-chloromethane in 250 ml of absolute acetonitrile are stirred with 13.6 g (0.2 mol) of imidazole for 3 hours at room temperature and thereafter heated to the boil for 15 minutes. The mixture is then concentrated and the dark brown residue is washed with water and taken up in methylene chloride. After drying with sodium sulphate, treating with active charcoal and filtering, the solution is concentrated. The residue is extracted by boiling with petroleum ether, and the mixture is filtered and again concentrated. Finally, the material is recrystallised from a little acetonitrile. 17.0 g (40% of theory) of the compound of formula ##SPC9##

Workup

  1. temperatureheated to the boil for 15 minutes
  2. concentrationThe mixture is then concentrated
  3. washthe dark brown residue is washed with water
  4. dry with materialAfter drying with sodium sulphate
  5. additiontreating with active charcoal
  6. filtrationfiltering
  7. concentrationthe solution is concentrated
  8. extractionThe residue is extracted
  9. filtrationthe mixture is filtered
  10. concentrationagain concentrated
  11. customFinally, the material is recrystallised from a little acetonitrile

Sources & evidence

ORD record
ord-84e03b3b264142f8878d0ff8326fe953
Source dataset
uspto-grants-1976_01
Patent number
US03934014

Reaction notes

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