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

HRID 893630Notes

Reaction equation

HRID 893630 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)([O-])C.[K+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:22]3([N:25]4[CH:29]=[N:28][C:27]([Cl:30])=[N:26]4)[CH2:24][CH2:23]3)[CH2:21][O:20]2)=[CH:15][CH:14]=1>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:22]2([N:25]3[CH:29]=[N:28][C:27]([Cl:30])=[N:26]3)[CH2:24][CH2:23]2)([OH:20])[CH2:21][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 146972292-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxiraneHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

13 g (191 mmol) of imidazole and 1 g (9 mmol) of potassium tert. butoxide are initially introduced under a nitrogen atmosphere into 100 ml of acetonitrile under reflux and 18 g (61 mmol) of 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane dissolved in 30 ml of acetonitrile are added dropwise. The mixture is allowed to react under reflux conditions for 10 hours and the solvent is then evaporated in vacuo. The residue is taken up in ethyl acetate and washed with water. The solution is dried over sodium sulphate and the solvent is removed in vacuo. Chromatographic purification on silica gel (solvent: dichloromethane/ethanol=90/10) gives 7.1 g (32% of theory) of the title compound of m.p. 231° C.

Workup

  1. temperatureunder reflux
  2. additionare added dropwise
  3. customto react under reflux conditions for 10 hours
  4. customthe solvent is then evaporated in vacuo
  5. washwashed with water
  6. dry with materialThe solution is dried over sodium sulphate
  7. customthe solvent is removed in vacuo
  8. customChromatographic purification on silica gel (solvent: dichloromethane/ethanol=90/10)

Sources & evidence

ORD record
ord-623017f287b64212b7e3622e3c6feebc
Source dataset
uspto-grants-1992_06
Patent number
US05126359

Reaction notes

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