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

HRID 893629Notes

Reaction equation

HRID 893629 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N: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>CN(C)C=O>[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]=[N:4][CH:3]=[N:2]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 146972292-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxiraneHCID 23665647Potassium tert-butoxide

Product 1

HCID 146972301-(4-Chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(1,2,4-triazol-1-yl)-ethan-1-olYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15.6 g (0.276 mol) of 1,2,4-triazole and 1.7 g (0.015 mol) of potassium tert. butoxide are initially introduced into 40 ml of abs. dimethylformamide and 21 g (0.071 mol) of 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane in 30 ml of absolute dimethylformamide are added dropwise at 80° C. The mixture is allowed to react at 100° C. for 6 hours and the solvent is then evaporated in vacuo. The residue is taken up in ethyl acetate/toluene, the solution is washed with water and dried over sodium sulphate, and the solvent is stripped off in vacuo. Chromatography on silica gel (eluent dichloromethane/ethanol =98/2) yields 11.5 g of the title compound of m.p. 156° C.

Workup

  1. customto react at 100° C. for 6 hours
  2. customthe solvent is then evaporated in vacuo
  3. washthe solution is washed with water
  4. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-f6156a7d2beb477e968002fde6217e1c
Source dataset
uspto-grants-1992_06
Patent number
US05126359

Reaction notes

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