Hydrochloric Acid → HCID 15979664, compound

HRID 1443585Notes

Reaction equation

HRID 1443585 reaction equation
[F:1][C:2]([F:18])([C:9]([F:17])([F:16])[C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])[CH2:3][CH:4]([C:7]#[N:8])[C:5]#[N:6].FC(F)(F)S(O[CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])(=O)=O.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[F:1][C:2]([F:18])([C:9]([F:16])([F:17])[C:10]([F:14])([F:15])[CH:11]([F:13])[F:12])[CH2:3][C:4]([CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])([C:7]#[N:8])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27760192,2,3,3,3-Pentafluoropropyl trifluoromethanesulfonateHCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

Product 1

HCID 15979664HCID 15979664, compoundYield 2.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 20 ml of acetone, 2.8 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile and 4.5 g of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonate were dissolved, 2.2 g of potassium carbonate was added and the mixture was stirred at room temperature for 8 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture and the mixture was extracted with t-butyl methyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.10 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(2,2,3,3,3-pentafluoropropyl)malononitrile (hereinafter, referred to as the present compound (91)).

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd938740c8934094b218912d13290f95
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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