Potassium Carbonate → HCID 22324281, compound

HRID 583820Notes

Reaction equation

HRID 583820 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1[S:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178418431pyridine-4-thiol

Product 1

HCID 22324281HCID 22324281, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

21 g (188.9 mmol) of 4-mercaptopyridine, 30.05 g (188.9 mmol) of 3,4-difluoro-nitrobenzene and 60.05 g (434.5 mmol) of potassium carbonate are dissolved in dimethylformamide, and the mixture is stirred at 40° C. for 3 hours. The reaction solution is then diluted with 500 mL of ethyl acetate and 300 mL of water. The aqueous phase is extracted five times with in each case 100 mL of ethyl acetate. The combined organic phases are washed with 200 mL of saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure using a rotary evaporator. The residue is purified by MPLC (mobile phase: ethyl acetate:cyclohexane 1:1).

Workup

  1. extractionThe aqueous phase is extracted five times with in each case 100 mL of ethyl acetate
  2. washThe combined organic phases are washed with 200 mL of saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customa rotary evaporator
  6. customThe residue is purified by MPLC (mobile phase: ethyl acetate:cyclohexane 1:1)

Sources & evidence

ORD record
ord-5bef5a8277794de1a9f9a81cf3ccb7f3
Source dataset
uspto-grants-2005_08
Patent number
US06924290B2

Reaction notes

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