Potassium Carbonate → HCID 18459339, compound

HRID 2305000Notes

Reaction equation

HRID 2305000 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[CH:37]=[CH:36][C:34]([O-:35])=[CH:33][C:32]=1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([O-:30])=[O:29].[K+].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[K+]>CS(C)=O>[N+:28]([C:31]1[CH:37]=[CH:36][C:34]([O:35][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])=[CH:33][C:32]=1[O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 11781031HCID 11781031, compoundHCID 184593372-(4-Benzyloxycarbonylphenoxy)-3,4,5,6-tetrafluoropyridine

Product 1

HCID 18459339HCID 18459339, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40 g of the 2-(4-benzyloxycarbonylphenoxy)-3,4,5,6-tetrafluoropyridine prepared as described in Example 6 (0.106 mol) and 30 g of potassium 4-nitro-3-benzyloxyphenoxide (0.106 mol) are dissolved in 500 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, then heated at 60° C. for 24 hours, and 15 g of potassium hydrogencarbonate (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. temperatureheated at 60° C. for 24 hours
  2. temperatureThe reaction solution is then cooled to room temperature
  3. filtrationfiltered through
  4. filtrationa fluted filter
  5. washThe crude product is washed
  6. stirringby shaking with 300 ml of ethyl acetate and 700 ml of water
  7. washthe organic phase is washed three times with water
  8. customevaporated in a rotary evaporator until the reaction product
  9. customprecipitates out
  10. customThe reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1)
  11. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  12. customdrying cabinet (yield: 92%)

Sources & evidence

ORD record
ord-39f3119ce2da43b18e60b986cbbd472d
Source dataset
uspto-grants-2002_08
Patent number
US06437178B2

Reaction notes

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