1H-1,2,4-Triazole → HCID 20070417, compound

HRID 981537Notes

Reaction equation

HRID 981537 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][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)=[N:6][CH:7]=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:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=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 20070407HCID 20070407, compound

Product 1

HCID 20070417HCID 20070417, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[5-chloropyrid-2-yl]-2-[1-(1H-1,2,4-triazol-1-yl)ethyl]oxirane (70 mg; 0.28 m.Mole) in dimethylformamide (5 ml) was added 1,2,4-triazole (39 mg; 0.56 m.Mole) and anhydrous potassium carbonate (39 mg; 0.28 m.Mole). Heating, with stirring, was carried out for three hours at 80°. The solvent was then evaporated, water (20 ml.) was added, and the mixture was extracted with methylene chloride (3×10 ml). The combined organic extracts were washed with water (3×5 ml), dried over anhydrous magnesium sulphate, and evaporated to an oil (100 mg). Purification was carried out using a flash column of Merck "Kieselgel 60" 230-400 mesh silica, eluting with methylene chloride containing gradually increasing amounts of methanol (from 1 to 5%). The appropriate fractions, on evaporation, gave the pure title compound, 25 mg; m.p. 156°-157° (28.1% yield).

Workup

  1. temperatureHeating
  2. customThe solvent was then evaporated
  3. additionwater (20 ml.) was added
  4. extractionthe mixture was extracted with methylene chloride (3×10 ml)
  5. washThe combined organic extracts were washed with water (3×5 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to an oil (100 mg)
  8. customPurification
  9. washeluting with methylene chloride containing gradually increasing amounts of methanol (from 1 to 5%)
  10. customThe appropriate fractions, on evaporation

Sources & evidence

ORD record
ord-cc76391adc76427b833d0cc948cfac2a
Source dataset
uspto-grants-1991_02
Patent number
US04992454

Reaction notes

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