Sulfuric Acid → HCID 86644424, compound

HRID 2404504Notes

Reaction equation

HRID 2404504 reaction equation
C([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]([O:24][C:25]([F:33])([F:32])[CH:26]([F:31])[C:27]([F:30])([F:29])[F:28])[CH:6]=1)(=O)C.S(=O)(=O)(O)O>C(O)C.O>[NH2:4][C:5]1[N:9]([C:10]2[CH:15]=[C:14]([S:16][CH2:17][C:18]([F:20])([F:21])[F:19])[C:13]([CH3:22])=[CH:12][C:11]=2[F:23])[N:8]=[C:7]([O:24][C:25]([F:32])([F:33])[CH:26]([F:31])[C:27]([F:28])([F:29])[F:30])[CH:6]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 86644425HCID 86644425, compound

Product 1

HCID 86644424HCID 86644424, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.2 g of 5-acetylamino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)pyrazole was dissolved in 50 mL of ethanol, and an aqueous solution comprising 0.5 g of concentrated sulfuric acid in 2.0 mL of water was added, followed by reflux with heating for 6 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, and 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 0.9 g of 5-amino-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-(1,1,2,3,3,3-hexafluoropropoxy)pyrazole.

Workup

  1. additionwas added
  2. temperatureby reflux
  3. temperaturewith heating for 6 hours
  4. distillationthe solvent was distilled off under reduced pressure, and extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-599c6ba4dd25462999c62f28c8fac04b
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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