1-Methylimidazole → HCID 12983283, compound

HRID 493019Notes

Reaction equation

HRID 493019 reaction equation
[N-:1]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[F:16][C:17]([F:28])([F:27])[CH2:18][I+]C1C=CC(F)=CC=1.[CH3:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>C(Cl)Cl>[N-:1]([S:2]([C:5]([F:8])([F:6])[F:7])(=[O:4])=[O:3])[S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10].[CH3:29][N+:30]1[CH:34]=[CH:33][N:32]([CH2:18][C:17]([F:16])([F:27])[F:28])[CH:31]=1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 131727443HCID 131727443, compound

Product 1

HCID 12983283HCID 12983283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,2,2-Trifluoroethyl)(4-fluorophenyl)iodonium bis(trifluoromethanesulfonyl)imide (17.6 g, 30 mmol) and methylene chloride (60 ml) were placed in a reaction vessel to convert the inside of the reaction vessel to a nitrogen atmosphere. While stirring and cooling in an ice bath, 1-methylimidazole (2.46 g, 30 mmol) was added dropwise thereto. After the dropwise addition thereof, the ice bath was removed, and the mixture was allowed to react at room temperature for 3 hours. After the completion of the reaction, the solvent was removed by distillation. The resulting liquid product was washed with hexane (or pentane), water, and then hexane (or pentane). Subsequently, this liquid product was dissolved in a small amount of ethyl acetate, and a large amount of ether was added thereto to separate the liquid product. The liquid product was separated from the solvent and then dried at 110° C. for 6 hours under reduced pressure using a vacuum pump. Thus, pure 1-methyl-3-(2′,2′,2′-trifluoroethyl)imidazolium bis(trifluoromethanesulfonyl)imide (compound 9) was obtained as a liquid substance (yield 11.5 g, 86%). When the product is colored, it may be subjected to decolorization with active carbon. Separately, p-fluoroiodobenzene was obtained from the aforementioned hexane (or pentane) wash in a substantially quantitative manner.

Workup

  1. temperaturecooling in an ice bath
  2. additionAfter the dropwise addition
  3. customthe ice bath was removed
  4. customto react at room temperature for 3 hours
  5. customAfter the completion of the reaction
  6. customthe solvent was removed by distillation
  7. washThe resulting liquid product was washed with hexane (or pentane), water
  8. dissolutionSubsequently, this liquid product was dissolved in a small amount of ethyl acetate
  9. additiona large amount of ether was added
  10. customto separate the liquid product
  11. customThe liquid product was separated from the solvent
  12. customdried at 110° C. for 6 hours under reduced pressure

Sources & evidence

ORD record
ord-6390edf9a05a470fb3f5f813969be8ee
Source dataset
uspto-grants-2009_05
Patent number
US07534509B2

Reaction notes

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