1H-1,2,4-Triazole → HCID 13075562, compound

HRID 2295994Notes

Reaction equation

HRID 2295994 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1.[F-].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[N:21]1[CH:25]=[N:24][CH:23]=[N:22]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 522689Potassium FluorideHCID 4465204HCID 4465204, compound

Product 1

HCID 13075562HCID 13075562, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

65 g (0.24 mole) of 3-(4-methoxyphenyl)-2-phenylacrylic acid methyl ester and 67.3 g (0.98 mole) of 1,2,4-triazole were heated under reflux in the presence of 1.1 g of tribenzo-(18)-crown-6 and 8.1 g of potassium fluoride in 1 liter of acetonitrile for 240 hours. The solvent was then distilled off in vacuo, 700 ml of water were added to the residue and the mixture was extracted three times with 250 ml of methylene chloride each time. The combined organic phases were dried over sodium sulphate and concentrated. The residue was dissolved in 200 ml of acetone. 12 g of 1,5-naphthalenedisulphonic acid in 50 ml of acetone were filtered in and the precipitate formed was filtered off. This precipitate was taken up in 150 ml of saturated sodium bicarbonate solution and the mixture was extracted twice by stirring with 250 ml of methylene chloride each time. The combined organic phases were washed with 100 ml of water, dried over sodium sulphate and concentrated. The residue was recrystallized from ethyl acetate. 9.8 g of 3-(4-methoxyphenyl)-2-phenyl-3-(1,2,4-triazol-1-yl)-propionic acid methyl ester of melting point 159°-161° C. were obtained.

Workup

  1. distillationThe solvent was then distilled off in vacuo, 700 ml of water
  2. additionwere added to the residue
  3. extractionthe mixture was extracted three times with 250 ml of methylene chloride each time
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 200 ml of acetone
  7. filtration12 g of 1,5-naphthalenedisulphonic acid in 50 ml of acetone were filtered in and the precipitate
  8. customformed
  9. filtrationwas filtered off
  10. extractionthe mixture was extracted twice
  11. washThe combined organic phases were washed with 100 ml of water
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated
  14. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a2f86d0d6ae84a1f843ab55c5fa76392
Source dataset
uspto-grants-1984_01
Patent number
US04427673

Reaction notes

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