Hydrochloric Acid → HCID 86642965, compound

HRID 888642Notes

Reaction equation

HRID 888642 reaction equation
C1(C)C=CC(S([O:10][CH2:11][CH2:12][C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])(=O)=O)=CC=1.[C:27]([O-])(=[S:29])[CH3:28].[K+].Cl>CN(C)C=O>[C:27]([O:10][CH2:11][CH2:12][C:13]([F:24])([F:25])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:17])([F:18])[F:19])(=[S:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23670855Potassium ethanethioateHCID 866429663,3,4,4,5,5,6,6,6-Nonafluorohexyl 4-methylbenzene-1-sulfonate

Product 1

HCID 86642965HCID 86642965, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 42.65 g of 3,3,4,4,5,5,6,6,6-nonafluorohexyl p-toluenesulfonate, 100 ml of N,N-dimethylformamide and 11.65 g of potassium thioacetate was heated and stirred at 80° C. for 4 hours under a nitrogen atmosphere. A reaction vessel was cooled in an ice bath. To the reaction mixture was added an aqueous 1N hydrochloric acid solution, and the mixture was extracted with 200 ml of ethylacetate twice. Organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 18.91 g of 3,3,4,4,5,5,6,6,6-nonafluorohexyl thioacetate represented by the formula:

Workup

  1. temperaturewas heated
  2. temperatureA reaction vessel was cooled in an ice bath
  3. extractionthe mixture was extracted with 200 ml of ethylacetate twice
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07e0b8b6ba364377a58e751349812a6d
Source dataset
uspto-grants-2012_08
Patent number
US08247596B2

Reaction notes

Loading…