Acetic Acid → HCID 15454653, compound

HRID 279168Notes

Reaction equation

HRID 279168 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[NH:15][NH2:16])=[CH:9][CH:8]=2)[N:5]=[CH:4][N:3]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:20][CH:19]=1.[CH3:32]N(C)C=O.C(O)(=O)C.C(O)(=O)C.C(N)=N>O>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:32]=[N:16][NH:15][C:14]3=[O:17])=[CH:9][CH:8]=2)[N:5]=[CH:4][N:3]1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([F:30])([F:31])[CH:27]([F:28])[F:29])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 160693Formamidine acetateHCID 22624542HCID 22624542, compound

Product 1

HCID 15454653HCID 15454653, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[4-[5-Oxo-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-1H,4H-1,2,4-triazol-1-yl]phenyl]semicarbazide (4.75 g) was added to N,N-dimethylformamide (60 ml). To the mixture were added acetic acid (4 g) and formamidine acetate (6 g), and the resulting mixture was stirred at room temperature for 3 hours and then at 80° C. for 1.5 hours. After cooling, the reaction solution was diluted with water (30 ml). The precipitated crystals were collected by filtration and washed with water (100 ml). The crystals were dried and dissolved in a mixture of tetrahydrofuran (300 ml) and ethyl acetate (600 ml) with warming. The solution thus obtained was dried over anhydrous magnesium sulfate, filtrated and concentrated under reduced pressure. Ethyl acetate (50 ml) was added to the residue and the precipitated crystals were collected by filtration and recrystallized from tetrahydrofuran to give 4-[4-[5-oxo-4-[4-(2,2,3,3-tetrafluoropropoxy)-phenyl]-1H,4H-1,2,4-triazol-1-yl]phenyl]-3(2H,4H)-1,2,4-triazolone (2.4 g, 49%) as a white crystalline powder.

Workup

  1. waitat 80° C. for 1.5 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water (100 ml)
  5. customThe crystals were dried
  6. dissolutiondissolved in a mixture of tetrahydrofuran (300 ml) and ethyl acetate (600 ml)
  7. temperaturewith warming
  8. customThe solution thus obtained
  9. dry with materialwas dried over anhydrous magnesium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated under reduced pressure
  12. additionEthyl acetate (50 ml) was added to the residue
  13. filtrationthe precipitated crystals were collected by filtration
  14. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-147f53f3d88d49009d02c6e959976986
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

Loading…