Sodium Dithionite → HCID 12115483, compound

HRID 2373334Notes

Reaction equation

HRID 2373334 reaction equation
[CH3:1][CH:2]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].[F:15][C:16](I)([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18].C(=O)([O-])O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.O.COC(C)(C)C>[CH3:1][CH:2]([C:8]1[CH:14]=[C:13]([C:16]([F:15])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])[CH:12]=[CH:11][C:9]=1[NH2:10])[CH2:3][CH2:4][CH:5]([CH3:6])[CH3:7]

Participants

9

Reactant 4

HCID 24489Sodium DithioniteHCID 33978Perfluoroisopropyl iodideHCID 516892Sodium BicarbonateHCID 12115482HCID 12115482, compound

Product 1

HCID 12115483HCID 12115483, compoundYield 97.1%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8058HexaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

The 2-(1,4-dimethylpentyl)aniline (1.8 g, 9.4 mmol) obtained in Example 3-2 was dissolved in a solution (50 ml) consisting of t-butyl methyl ether and water in the ratio of 1:1. To the resulting solution were added 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl iodide (2.78 g, 9.4 mmol), tetra-n-butylammonium hydrogensulfate (318 mg, 0.94 mmol), sodium hydrogencarbonate (795 mg, 9.4 mmol) and then sodium dithionite (1.63 g, 9.4 mmol), and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with hexane and washed twice with 3N hydrochloric acid and then with an aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain 3.28 g of the desired compound.

Workup

  1. washwashed twice with 3N hydrochloric acid
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4e3dde80f364401a1525760271ddd1c
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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