Imidazole → 1-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane

HRID 844555Notes

Reaction equation

HRID 844555 reaction equation
CS(O[CH2:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:8][CH:9]1[O:13][CH2:12][CH2:11][O:10]1)(=O)=O.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>C(#N)C>[N:22]1([CH2:6][CH:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:8][CH:9]2[O:13][CH2:12][CH2:11][O:10]2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 226137911-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane

Product 1

HCID 226138091-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propaneYield 77.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane (15.5 g) (see Preparation 16) and imidazole (9 g) were dissolved in anhydrous acetonitrile (100 ml) and the mixture heated at reflux for 90 hours. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane (100 ml) and the solvent again removed under reduced pressure. The residue was dissolved in dichloromethane (300 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 then combined and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel, eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane:methanol to give 1-(imidazol-1-yl)-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane (11.1 g) as an orange oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 90 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane (100 ml)
  5. customthe solvent again removed under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane (300 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
  13. washeluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane

Sources & evidence

ORD record
ord-eccd433391924b1e95d1d9d458467f07
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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