Iodopentafluoroethane → HCID 10400765, compound

HRID 1359624Notes

Reaction equation

HRID 1359624 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:12][C:13](I)([F:18])[C:14]([F:17])([F:16])[F:15].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH2:9])=[C:10]([C:13]([F:18])([F:12])[C:14]([F:17])([F:16])[F:15])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 9636IodopentafluoroethaneHCID 24489Sodium DithioniteHCID 698614-Tert-ButylanilineHCID 516892Sodium BicarbonateHCID 11433187Bis(tetrabutylammonium) sulphate

Product 1

HCID 10400765HCID 10400765, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a liquid mixture of 40 ml of water and 40 ml of ethyl acetate were successively added 2.2 g of 4-tert-butylaniline, 5.0 g of perfluoroethyl iodide, 3.1 g of sodium dithionite, 1.5 g of sodium hydrogen carbonate and 0.6 g of tetrabutylammonium sulfate, and the resulting mixture was stirred at room temperature for 15 hours. The organic layer was separated, then the aqueous layer was extracted with 20 ml of ethyl acetate, and the organic layer were combined and washed successively with 2N aqueous hydrochloric acid, 5% aqueous sodium carbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried with magnesium sulfate, then filtered, the organic solvent was distilled off under reduced pressure and the residue was purified by column chromatography to obtain 0.7 g of the intended product. Yield: 18%

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 20 ml of ethyl acetate
  3. washwashed successively with 2N aqueous hydrochloric acid, 5% aqueous sodium carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. distillationthe organic solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-43508cab97bb47688eacc503970a1322
Source dataset
uspto-grants-2003_07
Patent number
US06600074B2

Reaction notes

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