Methyl iodide → 4-Chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketone

HRID 981538Notes

Reaction equation

HRID 981538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH:9]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19]I>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]([CH3:19])([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 155929311-(4-Chloro-phenyl)-2-[1,2,4]triazol-1-yl-propan-1-one

Product 1

HCID 133668554-Chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketoneYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

4'-Chloro-2-(1H-1,2,4-triazol-1-yl)propiophenone (2 g.) in dry tetrahydrofuran (30 ml) was added to a suspension of sodium hydride (480 mg. of a 60% dispersion in oil) in dry tetrahydrofuran (20 ml) at 0° under a nitrogen atmosphere. After stirring for 10 minutes, methyl iodide (2.28 g.) in dry tetrahydrofuran (10 ml.) was added dropwise and the reaction mixture was then stirred at 0° for 1 hour and then at room temperature overnight. The reaction mixture was then diluted with water (20 ml), extracted with ether (3×25 ml), and the combined organic extracts were washed with water and dried (MgSO4). The residue obtained after removal of the solvent was flash chromatographed on silica (150 g.) using ethyl acetate/hexane/diethylamine (50:50:3 v/v/v) for elution and the product-containing fractions on evaporation followed by crystallisation of the residue from ethyl acetate/hexane furnished the title compound, (1.68 g., 84% yield), m.p. 118°-9°.

Workup

  1. customat 0°
  2. stirringthe reaction mixture was then stirred at 0° for 1 hour
  3. customat room temperature
  4. customovernight
  5. extractionextracted with ether (3×25 ml)
  6. washthe combined organic extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customThe residue obtained
  9. customafter removal of the solvent
  10. customchromatographed on silica (150 g.)
  11. washfor elution
  12. customthe product-containing fractions on evaporation
  13. customfollowed by crystallisation of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3fb492847fed4ab18050ecefa5440f88
Source dataset
uspto-grants-1991_02
Patent number
US04992454

Reaction notes

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