Acetonitrile → 1-(1-Chlorocyclopropyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

HRID 1655939Notes

Reaction equation

HRID 1655939 reaction equation
Cl[CH2:2][C:3]([C:5]1([Cl:8])[CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].N1C=[CH:18][N:17]=[N:16]1.[C:20](#[N:22])C>>[Cl:8][C:5]1([C:3](=[O:4])[CH2:2][N:17]2[CH:18]=[N:22][CH:20]=[N:16]2)[CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 11062580Ethanone, 2-chloro-1-(1-chlorocyclopropyl)-HCID 178418936HCID 178418936, compound

Product 1

HCID 143483801-(1-Chlorocyclopropyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-oneYield 51%

Procedure

100 g (0.66 mol) of 1-chloro-cyclopropyl chloromethyl ketone in 80 ml of acetonitrile are added dropwise to a refluxing suspension of 83 g (0.6 mol) of potassium carbonate and 58 g (0.84 mol) of triazole in 330 ml of acetonitrile. The mixture is refluxed for 8 hours and then filtered off with suction and concentrated. The residue is taken up in ethyl acetate/toluene, and the mixture is washed with water, dried over sodium sulphate and concentrated. The subsequent purification by column chromatography in which dichloromethane was used as the mobile phase gave 62 g (51% of theory) of 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)-ethan-1-one.

Workup

  1. temperatureThe mixture is refluxed for 8 hours
  2. filtrationfiltered off with suction
  3. concentrationconcentrated
  4. washthe mixture is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe subsequent purification by column chromatography in which dichloromethane

Sources & evidence

ORD record
ord-e4ddf562c8f5457b9397b38d6a8c2b6a
Source dataset
uspto-grants-1993_10
Patent number
US05252582

Reaction notes

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