1-Methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium iodide → 1-Methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium 1,1,2,2-tetrafluoroethanesulfonate

HRID 1985583Notes

Reaction equation

HRID 1985583 reaction equation
[F:1][C:2]([F:10])([S:6]([O-:9])(=[O:8])=[O:7])[CH:3]([F:5])[F:4].[K+].[I-].[CH3:13][N+:14]1[CH:18]=[CH:17][N:16]([CH2:19][CH2:20][C:21]([F:39])([F:38])[C:22]([F:37])([F:36])[C:23]([F:35])([F:34])[C:24]([F:33])([F:32])[C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27])[CH:15]=1>CC(C)=O>[F:1][C:2]([F:10])([S:6]([O-:9])(=[O:8])=[O:7])[CH:3]([F:5])[F:4].[CH3:13][N+:14]1[CH:18]=[CH:17][N:16]([CH2:19][CH2:20][C:21]([F:38])([F:39])[C:22]([F:36])([F:37])[C:23]([F:34])([F:35])[C:24]([F:32])([F:33])[C:25]([F:30])([F:31])[C:26]([F:27])([F:28])[F:29])[CH:15]=1

Participants

4

Reactant 2

HCID 154950931-Methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium iodideHCID 58905542Potassium 1,1,2,2-tetrafluoroethanesulfonate

Product 1

HCID 866115671-Methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium 1,1,2,2-tetrafluoroethanesulfonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1-Methylimidazole (4.32 g, 0.52 mol) was partially dissolved in reagent-grade toluene (50 ml) in a large round-bottomed flask and stirred vigorously. 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (26 g, 0.053 mol) was added, and the mixture was heated under reflux at 110° C. for 24 hours. The solvent was removed under vacuum giving 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium iodide (30.5 g) as a waxy solid. Potassium 1,1,2,2-tetrafluoroethanesulfonate (TFES-K, 12 g) was added to reagent grade acetone (100 ml) in a separate round-bottomed flask, and this solution was carefully added to the 1-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium iodide which had been dissolved in acetone (50 ml). The reaction mixture was heated under reflux for approximately 16 hours. The reaction mixture was then filtered using a large frit glass funnel to remove the white KI precipitate formed, and the filtrate was placed on a rotary evaporator for 4 hours to remove the acetone. The oily liquid was then filtered a second time to yield the product, as shown by proton NMR.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for approximately 16 hours
  3. filtrationThe reaction mixture was then filtered
  4. customto remove the white KI precipitate
  5. customformed
  6. customthe filtrate was placed on a rotary evaporator for 4 hours
  7. customto remove the acetone
  8. filtrationThe oily liquid was then filtered a second time
  9. customto yield the product

Sources & evidence

ORD record
ord-fe7a79b84b2d45fda67980d018b6a06c
Source dataset
uspto-grants-2009_06
Patent number
US07544813B2

Reaction notes

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