1H-1,2,4-Triazole → HCID 15593720, compound

HRID 981542Notes

Reaction equation

HRID 981542 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)([CH3:13])[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:19]1([CH2:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([OH:9])[C:11]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)([CH3:13])[CH3:12])[CH:23]=[N:22][CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 20070410HCID 20070410, compound

Product 1

HCID 15593720HCID 15593720, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-2-[2-(1H-1,2,4-triazol-1-yl)prop-2-yl]oxirane (1.0 g, 4.0 mMole) in dimethylformamide (50 ml) were added 1,2,4-triazole (0.56 g., 8.0 mMole) and anhydrous potassium carbonate (0.56 g, 4.0 mMole). Heating at 80°, with stirring, was carried out for 19 hours. The solvent was then evaporated, water (75 ml) was added, and the mixture was extracted with methylene chloride (3×50 ml.). The combined organic extracts were washed with water (3×30 ml), dried over anhydrous magnesium sulphate, and evaporated to an impure gum (1.15 g). Purification of the gum was carried out using a flash column of Merck "Kieselgel 60" (Trademark) 230-400 mesh silica eluting with methylene chloride and 5% methanol in methylene chloride. The appropriate fractions on evaporation gave a solid which was recrystallised from diisopropylether and isopropyl alcohol giving the title compound, 0.4 g., m.p. 156°-158° (31.9% yield).

Workup

  1. temperatureHeating at 80°
  2. customThe solvent was then evaporated
  3. additionwater (75 ml) was added
  4. extractionthe mixture was extracted with methylene chloride (3×50 ml.)
  5. washThe combined organic extracts were washed with water (3×30 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to an impure gum (1.15 g)
  8. customPurification of the gum
  9. customThe appropriate fractions on evaporation
  10. customgave a solid which
  11. customwas recrystallised from diisopropylether and isopropyl alcohol giving the title compound, 0.4 g

Sources & evidence

ORD record
ord-4e1d4844929742c88c03586c70d1017a
Source dataset
uspto-grants-1991_02
Patent number
US04992454

Reaction notes

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