Sodium Iodide → N-butyl-5-iodo-N-methyl-pentanesulfonamide

HRID 724805Notes

Reaction equation

HRID 724805 reaction equation
[I-:1].[Na+].[CH2:3]([N:7]([CH3:17])[S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Cl)(=[O:10])=[O:9])[CH2:4][CH2:5][CH3:6]>C(C(C)=O)C>[CH2:3]([N:7]([CH3:17])[S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][I:1])(=[O:10])=[O:9])[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19711033N-butyl-5-chloro-N-methyl-pentanesulfonamide

Product 1

HCID 19711034N-butyl-5-iodo-N-methyl-pentanesulfonamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

526 mg of sodium iodide were added to a solution of 449 mg of the product of Step A in 4.5 ml of methyl ethyl ketone, and the mixture was stirred at reflux for 4 hours. After cooling, the methyl ethyl ketone was evaporated under reduced pressure and water was added. Extraction was carried out with ethyl acetate and the extracts were washed with water, then with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness under reduced pressure to obtain 572 mg of the expected product.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureAfter cooling
  3. customthe methyl ethyl ketone was evaporated under reduced pressure and water
  4. additionwas added
  5. extractionExtraction
  6. washthe extracts were washed with water
  7. dry with materialwith a saturated aqueous solution of sodium chloride, dried
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fd4eaacb7c4b48f094e42c9e2a6e7461
Source dataset
uspto-grants-1998_01
Patent number
US05705494

Reaction notes

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