Aniline → HCID 58297498, compound

HRID 590912Notes

Reaction equation

HRID 590912 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].[F:21][C:22]([F:34])([F:33])[C:23]([F:32])([F:31])[C:24](I)([F:29])[C:25]([F:28])([F:27])[F:26]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.COC(C)(C)C>[F:26][C:25]([F:27])([F:28])[C:24]([F:29])([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[C:23]([F:31])([F:32])[C:22]([F:34])([F:33])[F:21]

Participants

8

Reactant 4

HCID 6115AnilineHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 27751652-Iodoperfluorobutane

Product 1

HCID 58297498HCID 58297498, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4.90 g (52.6 mmol) of aniline, 10.1 g (58.0 mmol) of 85% sodium hydrosulfite, and 1.90 g (5.77 mmol) of tetrabutylammonium hydrogen sulfate were charged to a mixed solution of 150 ml of t-butyl methyl ether and 150 ml of water using a light-shielded reaction vessel, and 4.84 g (57.6 mmol) of sodium hydrogen carbonate was added thereto. 20.0 g (57.8 mmol) of nonafluoro-s-butyliodide was added dropwise thereto at room temperature, followed by stirring at room temperature for 5 hours. The organic phase was collected by separation, washed with 2 mol/L of an aqueous hydrochloric acid solution twice, and then washed with saturated brine, an aqueous sodium hydrogen carbonate solution, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to prepare 8.32 g (yield 51%) of a target compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. customThe organic phase was collected by separation
  4. washwashed with 2 mol/L of an aqueous hydrochloric acid solution twice
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4c41f60459c64c8f9d0acdb9337f773f
Source dataset
uspto-grants-2016_01
Patent number
US09237745B2

Reaction notes

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