Water → HCID 86644457, compound

HRID 2404528Notes

Reaction equation

HRID 2404528 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(=O)([O-])[O-].[K+].[K+].FC(F)(C(F)(F)F)C(F)(F)C(S(O[CH2:41][C:42]([F:56])([F:55])[O:43][C:44]([F:54])([F:53])[C:45]([O:48][C:49]([F:52])([F:51])[F:50])([F:47])[F:46])(=O)=O)(F)F.O>CS(C)=O.C(OCC)(=O)C>[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][CH2:41][C:42]([F:55])([F:56])[O:43][C:44]([F:53])([F:54])[C:45]([O:48][C:49]([F:50])([F:51])[F:52])([F:47])[F:46])[CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 86644458HCID 86644458, compoundHCID 178474353HCID 178474353, compound

Product 1

HCID 86644457HCID 86644457, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

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 0.28 g of potassium carbonate and 1.0 g of 2,2-difluoro-2-{2-trifluoromethoxy-(1,1,2,2-tetrafluoroethoxy)}ethyl nonafluorobutylsulfonate were added, followed by stirring at room temperature for 12 hours. After completion of the reaction, the reaction solution was poured into water, extraction with ethyl acetate was carried out, and after washing with a saturated salt solution, 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 (ethyl acetate:hexane=1:4) to obtain 0.67 g of 5-acetylamino-3-[2,2-difluoro-2-{2-trifluoromethoxy-(1,1,2,2-tetrafluoroethoxy)}ethoxy]-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}pyrazole.

Workup

  1. customAfter completion of the reaction
  2. washafter washing with a saturated salt solution
  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 (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-f9696951b94a48298e6f7dd3529c4805
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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