Sulfuric Acid → HCID 58297519, compound

HRID 2360377Notes

Reaction equation

HRID 2360377 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([F:22])([C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=1)[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].S(=O)(=O)(O)O.[I:30]N1C(=O)CCC1=O.[OH-].[Na+]>C(OCC)(=O)C.C(O)C>[I:30][C:16]1[CH:17]=[C:11]([C:3]([F:22])([C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6])[C:2]([F:23])([F:24])[F:1])[CH:12]=[C:13]([C:18]([F:19])([F:20])[F:21])[C:14]=1[NH2:15]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 120273N-IodosuccinimideHCID 58297518HCID 58297518, compound

Product 1

HCID 58297519HCID 58297519, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To 100 mL of ethanol was added 17.0 g (44.8 mmol) of 4-(perfluorobutan-2-yl)-2-(trifluoromethyl)aniline, and 5.28 g (53.8 mmol) of concentrated sulfuric acid and 12.6 g (55.8 mmol) of N-iodosuccinimide were added thereto under ice-cooling, followed by stirring at room temperature for 1 hour and 30 minutes and at 40° C. for 4 hours. To the reaction solution was added a 4 M aqueous sodium hydroxide solution to neutralize the reaction solution, and then ethyl acetate was added thereto to extract the organic phase. The organic phase was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=10:1) to prepare 14.6 g (yield 65%) of a target compound.

Workup

  1. additionwere added
  2. temperatureunder ice-cooling
  3. extractionto extract the organic phase
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-17960769591349c0ba9e06c7bf49bd3a
Source dataset
uspto-grants-2014_04
Patent number
US08686044B2

Reaction notes

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