Potassium Carbonate → HCID 86644471, compound

HRID 2404540Notes

Reaction equation

HRID 2404540 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:21])([F:20])[F:19])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([OH:24])[CH:6]=1)(=[O:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].[F:31][C:32]([F:55])([F:54])[C:33]([F:53])([F:52])[C:34]([F:51])([F:50])[C:35]([F:49])([F:48])S(OCC(F)(F)C(F)(F)F)(=O)=O>CS(C)=O>[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:19])([F:20])[F:21])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([O:24][CH2:25][C:35]([F:48])([F:49])[C:34]([F:50])([F:51])[C:33]([F:52])([F:53])[C:32]([F:31])([F:54])[F:55])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866246582,2,3,3,3-Pentafluoropropyl nonafluorobutane-1-sulfonateHCID 178474353HCID 178474353, compound

Product 1

HCID 86644471HCID 86644471, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.5 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-hydroxypyrazole was dissolved in 10 mL of dimethylsulfoxide, and 0.23 g of potassium carbonate was added, followed by stirring at room temperature for 5 minutes. To this solution, 0.79 g of 2,2,3,3,3-pentafluoropropyl nonafluorobutanesulfonate was added, followed by stirring at room temperature for 12 hours. Then, extraction with ethyl acetate was carried out, the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 0.55 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(2,2,3,3,4,4,5,5,5-nonafluoropentyloxy)pyrazole.

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. extractionThen, extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-a2219ae534c34cd1971d49cd6554683a
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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