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

HRID 1533037Notes

Reaction equation

HRID 1533037 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-7174fc6114f740a4a596adc0ebe154e3
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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