Imidazole → 4-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene

HRID 844562Notes

Reaction equation

HRID 844562 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13]OS(C)(=O)=O)[CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 226137984-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene

Product 1

HCID 226138214-(3,4-Dichlorophenyl)-5-(imidazol-1-yl)pent-1-eneYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene (5.4 g) (see Preparation 23) and imidazole (3.6 g) were dissolved in anhydrous acetonitrile (40 ml) and the mixture heated under reflux for 100 hours. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane (100 ml) and washed with sufficient aqueous sodium carbonate solution to ensure that the aqueous phase reached pH14. The two phases were separated and the aqueous phase extracted with dichloromethane (100 ml). The organic phases were combined and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with a solvent gradient of 100:0 changing to 98:2, by volume, dichloromethane:methanol, to give 4-(3,4-dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene (3.45 g) as an orange oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 100 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  7. washwashed with sufficient aqueous sodium carbonate solution
  8. customThe two phases were separated
  9. extractionthe aqueous phase extracted with dichloromethane (100 ml)
  10. customthe solvent removed under reduced pressure
  11. customto give a residue which
  12. customwas chromatographed on silica gel eluting with a solvent gradient of 100:0 changing to 98:2, by volume, dichloromethane

Sources & evidence

ORD record
ord-90e9a46f3ae9440c97946125090bbea9
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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