1-Methylimidazole → HCID 12983283, compound

HRID 493018Notes

Reaction equation

HRID 493018 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:27])([F:26])[CH2:18][I+]C1C=CC=CC=1.[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[CH:30]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].[CH3:28][N+:29]1[CH:33]=[CH:32][N:31]([CH2:18][C:17]([F:16])([F:26])[F:27])[CH:30]=1

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 11731435HCID 11731435, compound2×

Product 1

HCID 12983283HCID 12983283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,2,2-Trifluoroethyl)(phenyl)iodonium bis(trifluoromethanesulfonyl)imide (compound 7) (3.4 g, 6 mmol) and methylene chloride (12 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 (0.49 g, 6 mmol) was added dropwise thereto over the course of 1 minute. 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 water and then with hexane in order to remove a side product, iodobenzene. 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. 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 1.94 g, 73%). When the product is colored, it may be subjected to decolorization with active carbon. Physical property, elemental analysis and spectral data of the compound 9 are shown in Table 8.

Workup

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

Sources & evidence

ORD record
ord-b2965c939c8c477399a9b12287019690
Source dataset
uspto-grants-2009_05
Patent number
US07534509B2

Reaction notes

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