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

HRID 1533044Notes

Reaction equation

HRID 1533044 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.ClCCl.CO>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

6

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 6344DichloromethaneHCID 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 chrornatographed 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

Sources & evidence

ORD record
ord-54a78e6ecbe24bd29614ce852721b275
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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