Acetic Acid → HCID 19373627, compound

HRID 1491790Notes

Reaction equation

HRID 1491790 reaction equation
[F:1][C:2]([F:18])([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[NH:15][NH2:16])=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].Cl.[C:20](N)(=N)[CH3:21].C(O)(=O)C>CN(C)C=O>[CH3:20][C:21]1[N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:2]([F:18])([F:1])[CH:3]([F:4])[F:5])=[CH:12][CH:11]=2)[C:14](=[O:17])[NH:15][N:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67170Acetamidine monohydrochlorideHCID 10683230HCID 10683230, compound

Product 1

HCID 19373627HCID 19373627, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]semicarbazide (6.0 g) and 10.6 g of acetamidine hydrochloride were dissolved in 100 ml of dimethylformamide. The solution was stirred for one hour at room temperature. After adding 6.6 g of acetic acid, the reaction solution was heated at 80° C. for seven hours and concentrated under reduced pressure. The residue was dissolved in a mixture of 200 ml of ethyl acetate and 40 ml of water. The separated organic layer was washed with water and saturated sodium chloride solution, dried and distilled off to remove the solvent. The residue was recrystallized from ethyl acetate to give 3.6 g of 5-methyl-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3(2H,4H)-1,2,4-triazolone as colorless needles.

Workup

  1. temperaturethe reaction solution was heated at 80° C. for seven hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of 200 ml of ethyl acetate and 40 ml of water
  4. washThe separated organic layer was washed with water and saturated sodium chloride solution
  5. customdried
  6. distillationdistilled off
  7. customto remove the solvent
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3152f05ae05d4af695ec88748a6485e6
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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