1H-1,2,4-Triazole → HCID 14348252, compound

HRID 2164991Notes

Reaction equation

HRID 2164991 reaction equation
[Cl:1][C:2]1([C:5]2([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH2:7][O:6]2)[CH2:4][CH2:3]1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1([C:5]([OH:6])([CH2:7][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)[CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 14348251HCID 14348251, compound

Product 1

HCID 14348252HCID 14348252, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution 27.9 g (0.11 mol) of 2-(1-chlorocyclopropyl)-2-(4-chloro-phenoxymethyl)-oxirane in 50 ml of acetonitrile is added dropwise under a nitrogen atmosphere to a mixture of 29 g (0.42 mol) of 1,2,4-triazole, 19 g (0.14 mol) of potassium carbonate and 100 ml bf acetonitrile, and the reaction mixture is boiled under reflux. After completion of the addition, the mixture is heated for a further 8 hours under reflux. The mixture is then filtered off from the solid residue with suction and the filtrate is concentrated under reduced pressure. The remaining residue is taken up in ethyl acetate. The resultant solution is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The product thus obtained is purified chromatographically through silica gel using chloroform/ethanol=97:3 as eluent. In this manner, 13.7 g (39% of theory) of 2-(1-chlorocyclopropyl)-1-(4-chlorophenoxy)-3-(1,2,4-triazol-1-yl)-propan-2-ol are obtained in the form of an oil.

Workup

  1. temperatureunder reflux
  2. additionAfter completion of the addition
  3. temperaturethe mixture is heated for a further 8 hours
  4. temperatureunder reflux
  5. filtrationThe mixture is then filtered off from the solid residue with suction
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. washThe resultant solution is washed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customThe product thus obtained
  11. customis purified chromatographically through silica gel

Sources & evidence

ORD record
ord-bbf58365636f40e588b6d6ba2eff941f
Source dataset
uspto-grants-1990_07
Patent number
US04938791

Reaction notes

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