1H-1,2,4-Triazole → HCID 57132067, compound

HRID 1650795Notes

Reaction equation

HRID 1650795 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)CCl)=[N:6][CH:7]=1.[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1.[C:17](=[O:20])([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:17]([CH:8]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:20])[N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 230524982-Chloro-1-(5-chloropyridin-2-yl)ethan-1-one

Product 1

HCID 57132067HCID 57132067, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

5-Chloro-2-chloroacetylpyridine (20 g.) was dissolved in acetonitrile (25 ml.) and added dropwise to a refluxing solution of 1,2,4-triazole (6.2 g.) and potassium carbonate (13.4 g.) in acetonitrile (25 ml.). When the addition was complete, the solution was allowed to cool and was stirred for 2 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed twice with water and twice with brine, dried over sodium sulphate and filtered. The filtrate was evaporated to dryness under reduced pressure, and the residue was chromatographed on a K60 silica column, eluting with ethyl acetate, to give 5-chloropyrid-2-yl-1,2,4-triazol-1-ylmethyl ketone which after crystallisation from ethyl acetate/petroleum ether (b.p. 60°-80°), had m.p. 146°-148°.

Workup

  1. additionWhen the addition
  2. temperatureto cool
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe ethyl acetate layer was separated
  6. washwashed twice with water and twice with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness under reduced pressure
  10. customthe residue was chromatographed on a K60 silica column
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-2b5e18c6b85b4492b14aaeab6b66dbe8
Source dataset
uspto-grants-1990_05
Patent number
US04925863

Reaction notes

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