1H-1,2,4-Triazole → HCID 13366873, compound

HRID 981541Notes

Reaction equation

HRID 981541 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:11]([N:13]3[CH:17]=[N:16][CH:15]=[N:14]3)[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:18]1([CH2:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([OH:9])[CH:11]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH3:12])[CH:22]=[N:21][CH:20]=[N:19]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 20070408HCID 20070408, compound

Product 1

HCID 13366873HCID 13366873, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-2-[1-(1H-1,2,4-triazol-1-yl)ethyl]oxirane (0.5 g, 2.1 mMole) in dimethylformamide (30 ml) was added 1,2,4-triazole (0.29 g, 4.2 mMole) and anhydrous potassium carbonate (0.29 g, 2.1 mMole). Heating, with stirring, was carried out for three hours at 85°. The solvent was evaporated, water (65 ml) was added, and the mixture was then extracted with methylene chloride (3×20 ml). The combined organic extracts were washed with water (3×10 ml), dried over anhydrous magnesium sulphate and evaporated to a gum, (1.1 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 containing gradually increasing amounts of methanol (from 5 to 10%). The appropriate fractions, on evaporation, gave the title compound, 318 mg; m.p. 103°-106° (49.1% yield).

Workup

  1. temperatureHeating
  2. customThe solvent was evaporated
  3. additionwater (65 ml) was added
  4. extractionthe mixture was then extracted with methylene chloride (3×20 ml)
  5. washThe combined organic extracts were washed with water (3×10 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to a gum, (1.1 g)
  8. customPurification of the gum
  9. customThe appropriate fractions, on evaporation

Sources & evidence

ORD record
ord-c8f456082926412cae5a67628bb33673
Source dataset
uspto-grants-1991_02
Patent number
US04992454

Reaction notes

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