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

HRID 844583Notes

Reaction equation

HRID 844583 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H: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]([C@@H: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 540787524(S)-(3,4-dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene

Product 1

HCID 544025344(S)-(3,4-dichlorophenyl)-5-(imidazol-1-yl)pent-1-eneYield 63.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4(S)-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene (8.25 g) (see Preparation 93) and imidazole (5.3 g) were dissolved in anhydrous acetonitrile (80 ml) and the mixture heated under reflux for 6 days. The solvent was removed under reduced pressure to give a residue which was partitioned between diethyl ether and aqueous saturated sodium hydrogen carbonate solution (pH of the aqueous phase was kept >7). The phases were separated and the aqueous phase extracted with diethyl ether. The combined organic extracts were then washed with water, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel, eluting with a solvent gradient of 98:2 changing to 95:5, by volume, dichloromethane:methanol to give 4(S)-(3,4-dichlorophenyl)-5-(imidazol-1-yl)pent-1-ene (4.78 g) as an oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 6 days
  3. customThe solvent was removed under reduced pressure
  4. customto give a residue which
  5. customwas partitioned between diethyl ether and aqueous saturated sodium hydrogen carbonate solution (pH of the aqueous phase
  6. customThe phases were separated
  7. extractionthe aqueous phase extracted with diethyl ether
  8. washThe combined organic extracts were then washed with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. customthe solvent removed under reduced pressure
  11. customto give a residue which
  12. customwas chromatographed on silica gel
  13. washeluting with a solvent gradient of 98:2 changing to 95:5, by volume, dichloromethane

Sources & evidence

ORD record
ord-c56cf992caf64982b2ad9a734939fd04
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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