Water → HCID 12010419, compound

HRID 2271249Notes

Reaction equation

HRID 2271249 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[F:6][C:7]([F:17])([F:16])[S:8](N1C=CN=C1)(=[O:10])=[O:9].[Cl-].[CH2:19]([NH+:21]1[CH:25]=[CH:24][N:23]([CH3:26])[CH2:22]1)[CH3:20].O>C1COCC1>[CH2:19]([NH+:21]1[CH:25]=[CH:24][N:23]([CH3:26])[CH2:22]1)[CH3:20].[F:6][C:7]([F:17])([F:16])[S:8]([CH:2]([C:1]#[N:5])[C:3]#[N:4])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 973001-[(trifluoromethyl)sulphonyl]-1H-imidazoleHCID 66822491HCID 66822491, compound

Product 2

HCID 12010419HCID 12010419, compoundHCID 21125190HCID 21125190, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6.61 g of malononitrile (100 mmoles) in solution in 50 ml of THF at −20° C., there is added, in portions, 795 mg of lithium hydride LiH. After 2 hours at −20° C., there is added 20.14 g (100 mmoles) of 1-(trifluoromethanesulfonyl)imidazole) (commercially available from Fluka). The reaction was continued during 4 hours at −20° C., and during 48 hours at room temperature. The solvent was then evaporated and the residue was reclaimed in 60 ml of water. There is then added 14.66 g (100 mmoles) of 1-ethyl-3-methyl-1H-imidazolium chloride (commercially available from Aldrich) to the aqueous solution. A dense phase which is denser than water was immediately formed. This phase was recovered by extraction with dichloromethane. After evaporation of dichloromethane and drying under vacuum at 40° C. of the liquid obtained, a molten salt of 1-ethyl-3-methyl-1H-imidazolium of trifluoromethanesulfonylmalononitrile was obtained, with a purity characterized by a proton, carbon and fluorine RMN higher than 98%.

Workup

  1. waitThe reaction was continued during 4 hours at −20° C.
  2. waitduring 48 hours at room temperature
  3. customThe solvent was then evaporated
  4. customwas immediately formed
  5. customThis phase was recovered by extraction with dichloromethane
  6. customAfter evaporation of dichloromethane
  7. customdrying under vacuum at 40° C. of the liquid
  8. customobtained

Sources & evidence

ORD record
ord-61d896903a6043dfa988c16ec55da31a
Source dataset
uspto-grants-2001_12
Patent number
US06333425B1

Reaction notes

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