Potassium Carbonate → HCID 15869764, compound

HRID 1602050Notes

Reaction equation

HRID 1602050 reaction equation
F[C:2]1[N:7]=[C:6](F)[C:5]([F:9])=[C:4](F)[C:3]=1[F:11].[OH:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+]>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C>[F:9][C:5]1[C:6]([O:26][C:23]2[N:17]([CH3:13])[N:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[N:7][C:2]([O:12][C:13]2[N:17]([CH3:18])[N:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[C:3]([F:11])[C:4]=1[O:12][C:13]1[N:17]([CH3:18])[N:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69690PentafluoropyridineHCID 178481859HCID 178481859, compound

Product 1

HCID 15869764HCID 15869764, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 31347SulfolaneSolventHCID 22335286Ethyl acetate pentaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of pentafluoropyridine (16.9 g, 0.1 mol), 5-hydroxy-1-methyl-3-trifluoromethylpyrazole (potassium salt, 62 g, 0.33 mol), and potassium carbonate (45.5 g, 0.33 mol) in anhydrous sulfolane (70 ml) is heated to 80° C. for 4 hours and then to 100° C. for 3 hours. The reaction mixture is diluted with pentane/ethyl acetate (1/1 by volume). After filtration through a bed of silica gel the filtrate is washed 8 times with water. The organic layer is dried with anhydrous magnesium sulfate and filtered over silica gel. Now the solvent is removed and the residue is washed with diisopropyl ether. After drying, colorless crystals (39.1 g, 64% yield) of melting point 119° C. are obtained.

Workup

  1. filtrationAfter filtration through a bed of silica gel the filtrate
  2. washis washed 8 times with water
  3. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  4. filtrationfiltered over silica gel
  5. customNow the solvent is removed
  6. washthe residue is washed with diisopropyl ether
  7. customAfter drying

Sources & evidence

ORD record
ord-ce8d218a065a49ad9148bf8f137b476a
Source dataset
uspto-grants-1999_11
Patent number
US05981437

Reaction notes

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