Dimethyl Sulfoxide → HCID 15072335, compound

HRID 1760499Notes

Reaction equation

HRID 1760499 reaction equation
[CH3:1][NH:2][S:3]([C:6]([F:30])([F:29])[C:7]([F:28])([F:27])[C:8]([F:26])([F:25])[C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=[O:5])=[O:4].CS(C)=O.[OH-].[K+].[CH2:37](Br)[CH:38]=[CH2:39]>O>[C:6]([S:3]([N:2]([CH2:39][CH:38]=[CH2:37])[CH3:1])(=[O:5])=[O:4])([C:7]([C:8]([C:9]([C:10]([C:11]([C:12]([C:13]([F:16])([F:15])[F:14])([F:18])[F:17])([F:19])[F:20])([F:21])[F:22])([F:23])[F:24])([F:25])[F:26])([F:27])[F:28])([F:30])[F:29]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 3034468N-Methylperfluorooctanesulfonamide

Product 1

HCID 15072335HCID 15072335, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A one-liter three-neck flask equipped with magnetic stirring and an addition funnel was charged with 150 g of N-methylperfluorooctanesulfonamide and 570 g of dimethyl sulfoxide, and the mixture was stirred for a few minutes until the solid dissolved. To this stirred solution was added a solution of 25 g of potassium hydroxide in 25 g of water. This mixture was allowed to stir for 30 min, then 46 g of allyl bromide was added dropwise via the addition funnel. An exotherm was noted after a few minutes. The reaction mixture was allowed to stir for 5.5 hr, during which time a white solid precipitated from solution. This solid was isolated by filtration, washed with 350 mL dimethyl sulfoxide, and dissolved in 450 g of 1,1,2-trichlorotrifluoroethane. This solution was transferred to a separatory funnel, washed with four 200 mL portions of water, and dried over anhydrous sodium sulfate. After removal of solvent by distillation at atmospheric pressure, the product was vacuum distilled to yield 138 g of C8F17SO2N(CH3)CH2CH═CH2, b.p. 98° C. at 0.4 torr (50 Pa) to 105° C. at 0.7 torr (90 Pa). The product was a clear, almost colorless liquid which solidified to a white, waxy solid upon standing at room temperature.

Workup

  1. customA one-liter three-neck flask equipped
  2. stirringthe mixture was stirred for a few minutes until the solid
  3. dissolutiondissolved
  4. stirringto stir for 30 min
  5. waitAn exotherm was noted after a few minutes
  6. stirringto stir for 5.5 hr, during which time a white solid
  7. customprecipitated from solution
  8. customThis solid was isolated by filtration
  9. washwashed with 350 mL dimethyl sulfoxide
  10. dissolutiondissolved in 450 g of 1,1,2-trichlorotrifluoroethane
  11. customThis solution was transferred to a separatory funnel
  12. washwashed with four 200 mL portions of water
  13. dry with materialdried over anhydrous sodium sulfate
  14. customAfter removal of solvent
  15. distillationby distillation at atmospheric pressure
  16. distillationdistilled

Sources & evidence

ORD record
ord-47d58cadd6a44942b6f994355f42a246
Source dataset
uspto-grants-2005_01
Patent number
US06841079B2

Reaction notes

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