Imidazole → 1-(4-Chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(imidazol-1-yl)-ethan-1-ol

HRID 2371913Notes

Reaction equation

HRID 2371913 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:16]3([N:19]4[CH:23]=[N:22][C:21]([Cl:24])=[N:20]4)[CH2:18][CH2:17]3)[CH2:15][O:14]2)=[CH:9][CH:8]=1>C(#N)C>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:16]2([N:19]3[CH:23]=[N:22][C:21]([Cl:24])=[N:20]3)[CH2:18][CH2:17]2)([OH:14])[CH2:15][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 146972292-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxirane

Product 1

HCID 146972311-(4-Chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(imidazol-1-yl)-ethan-1-olYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 13 g (191 mmol) of imidazole and 1 g (9 mmol) of potassium tert.-butylate in 100 ml of acetonitrile is refluxed under a nitrogen atmosphere. To this mixture there is added dropwise a solution of 18 g (61 mmol) of 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane in 30 ml of acetonitrile. The reaction mixture is refluxed for a further 10 hours and then concentrated by stripping off the solvent under reduced pressure. The residue which remains is taken up in ethyl acetate and washed with water. The organic phase is dried over sodium sulphate and then concentrated by stripping off the solvent under reduced pressure. The residue which remains is chromatographed on silica gel using a mixture of dichloromethane/ethanol=90:10 as the eluent. Concentration of the eluate gives 7.1 g (32% of theory) of 1-(4-chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(imidazol-1-yl)-ethan-1-ol in the form of a solid of melting point 231° C.

Workup

  1. temperatureis refluxed under a nitrogen atmosphere
  2. temperatureThe reaction mixture is refluxed for a further 10 hours
  3. concentrationconcentrated
  4. washwashed with water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue which remains is chromatographed on silica gel using
  8. additiona mixture of dichloromethane/ethanol=90:10 as the eluent

Sources & evidence

ORD record
ord-5df8fcf2a8cd4856981931fd40983838
Source dataset
uspto-grants-1992_03
Patent number
US05096913

Reaction notes

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