Imidazole → 1-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane

HRID 844568Notes

Reaction equation

HRID 844568 reaction equation
CS(O[CH2:6][CH:7]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)(=O)=O.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:25]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 226138361-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane

Product 1

HCID 226138011-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butaneYield 32.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (10 g) (see Preparation 29), imidazole (2.07 g) and potassium carbonate (7.65 g) were dissolved in anhydrous acetonitrile (50 ml) and heated under reflux under a nitrogen atmosphere for 3 days. The organic solvent was then removed under reduced pressure and the resulting aqueous suspension partitioned between dichloromethane and water. The organic phase was separated, washed sequentially with water and brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure. The crude product was chromatographed on silica gel eluting with 95:5, by volume, dichloromethane:methanol to give 1-(imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (3 g) as an oil and as a mixture of diastereomers.

Workup

  1. temperatureheated
  2. temperatureunder reflux under a nitrogen atmosphere for 3 days
  3. customThe organic solvent was then removed under reduced pressure
  4. customthe resulting aqueous suspension partitioned between dichloromethane and water
  5. customThe organic phase was separated
  6. washwashed sequentially with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent removed under reduced pressure
  9. customThe crude product was chromatographed on silica gel eluting with 95:5, by volume, dichloromethane

Sources & evidence

ORD record
ord-88e8f54d086141acbddcb8b684560007
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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