Hydrochloric Acid → HCID 86612552, compound

HRID 1443566Notes

Reaction equation

HRID 1443566 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].I[CH2:20][CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24].C(=O)([O-])[O-].[K+].[K+].Cl>CS(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]([CH2:20][CH2:21][CH2:22][C:23]([F:26])([F:25])[F:24])([C:7]#[N:8])[C:5]#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27751891,1,1-Trifluoro-4-iodobutaneHCID 25242027(2,2,3,3,4,4,5,5-Octafluoropentyl)propanedinitrile

Product 1

HCID 86612552HCID 86612552, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.4 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)malononitrile and 1.2 g of 1-iodo-4,4,4-trifluorobutane were dissolved in 5 ml of dimethyl sulfoxide, 0.83 g of potassium carbonate was added, and the mixture was stirred at room temperature for 5 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with methyl tert-butyl 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 0.35 g of 2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(4,4,4-trifluorobutyl)malononitrile (hereinafter, referred to as the present compound (66)).

Workup

  1. extractionfollowed by extraction with methyl tert-butyl 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-ac6233ac91324b3ba0e8ad1380c297f7
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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