Potassium Carbonate → HCID 23295546, compound

HRID 1870625Notes

Reaction equation

HRID 1870625 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:27]=[CH:26][C:14]([O:15][C:16]2[C:21]([F:22])=[C:20](F)[C:19]([F:24])=[C:18]([F:25])[N:17]=2)=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:28]([C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([OH:39])=[C:33]([F:40])[C:32]=1F)([O-:30])=[O:29].C(=O)([O-])[O-:43].[K+].[K+].C(=O)([O-])O.[K+]>CS(C)=O>[N+:28]([C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([O:39][C:20]2[C:19]([F:24])=[C:18]([F:25])[N:17]=[C:16]([O:15][C:14]3[CH:13]=[CH:12][C:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[CH:27][CH:26]=3)[C:21]=2[F:22])=[C:33]([F:40])[C:32]=1[OH:43])([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 6110932,3,5,6-Tetrafluoro-4-nitrophenolHCID 18459337HCID 18459337, compound

Product 1

HCID 23295546HCID 23295546, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40 g of 2-(4-benzyloxycarbonylphenoxy)-3,4, 5, 6-tetrafluoropyridine prepared as described in Example 7 (0.106 mol) and 22.4 g of 4-nitrotetrafluorophenol prepared as described in Example 4 (0.106 mol) are dissolved in 400 ml of dimethyl sulfoxide. 30 g of potassium carbonate (0.22 mol) are added in portions to the solution. The mixture is then stirred at room temperature for 24 hours and then heated at 60° C. for 24 hours, and 15 g of potassium hydrogen carbonate (0.15 mol) are then added. The reaction solution is then cooled to room temperature and filtered through a fluted filter. The crude product is washed by shaking with 300 ml of ethyl acetate and 700 ml of water, and the organic phase is washed three times with water and evaporated in a rotary evaporator until the reaction product precipitates out. The reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (Yield: 92%).

Workup

  1. customprepared
  2. temperatureheated at 60° C. for 24 hours
  3. temperatureThe reaction solution is then cooled to room temperature
  4. filtrationfiltered through
  5. filtrationa fluted filter
  6. washThe crude product is washed
  7. stirringby shaking with 300 ml of ethyl acetate and 700 ml of water
  8. washthe organic phase is washed three times with water
  9. customevaporated in a rotary evaporator until the reaction product
  10. customprecipitates out
  11. customThe reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1)
  12. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  13. customdrying cabinet (Yield: 92%)

Sources & evidence

ORD record
ord-9db0e357342c4772a0028a2d68482bc9
Source dataset
uspto-grants-2000_08
Patent number
US06096921

Reaction notes

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