Sodium Iodide → N-(2,2,3,3,4,4,4-heptafluorobutyl)-5-iodo-N-methylpentanesulfonamide

HRID 724807Notes

Reaction equation

HRID 724807 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9]([N:12]([CH2:14][C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH3:13])(=[O:11])=[O:10]>C(C(C)=O)C>[F:23][C:15]([F:24])([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH2:14][N:12]([CH3:13])[S:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][I:1])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 197110325-chloro-N-(2,2,3,3,4,4,4-heptafluorobutyl)-N-methyl-pentanesulfonamide

Product 1

HCID 19711036N-(2,2,3,3,4,4,4-heptafluorobutyl)-5-iodo-N-methylpentanesulfonamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

300 mg of sodium iodide were added to a solution of 355 mg of the product of Step A in 3 ml of methyl ethyl ketone and the mixture was refluxed for 4 hours. After evaporation of the solvent, the residue was taken up in water and extracted with ethyl acetate. The extracts were washed with an aqueous solution of sodium thiosulfate, then of sodium chloride, and evaporated to dryness under reduced pressure to obtain 425 mg of the expected product in the form of a colourless oil which slowly crystallized.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customAfter evaporation of the solvent
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with an aqueous solution of sodium thiosulfate
  5. customof sodium chloride, and evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fef91c2b59dc4c0e95bb086bd9dfeb43
Source dataset
uspto-grants-1998_01
Patent number
US05705494

Reaction notes

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