Sodium Carbonate → HCID 86644462, compound

HRID 2404533Notes

Reaction equation

HRID 2404533 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([SH:16])[C:13]([CH3:17])=[CH:12][C:11]=2[F:18])[N:8]=[C:7]([O:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(O[CH2:43][C:44]([Cl:47])([F:46])[F:45])(=O)=O>CN(C)C=O>[C:1]([NH:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:43][C:44]([Cl:47])([F:46])[F:45])[C:13]([CH3:17])=[CH:12][C:11]=2[F:18])[N:8]=[C:7]([O:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 86644460HCID 86644460, compoundHCID 86644463HCID 86644463, compound

Product 1

HCID 86644462HCID 86644462, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 1.5 g of 5-acetylamino-1-(2-fluoro-4-methyl-5-mercaptophenyl)-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole was dissolved in 20 mL of dimethylformamide, and 0.32 g of sodium carbonate and 1.5 g of 2-chloro-2,2-difluoroethyl nonafluorobutanesulfonate were added, followed by stirring at room temperature for 12hours. 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, the obtained residue was purified by silica gel column chromatography (developing solvent ethyl acetate:hexane=1:4) to obtain 1.3 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2-chloro-2,2-difluoroethylthio)phenyl}-3-(2,2,3,3,3-pentafluoropropoxy)pyrazole.

Workup

  1. extractionThen, extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-85e6161200bc41729a565ee349f0b4bf
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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