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Acetonitrile → 1,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) 2-(3-(n,n-dimethylamino)propylamino)succinate

HRID 352716
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 352716
[C:1]([O:23][CH2:24][CH2:25][C:26]([F:38])([F:37])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=[O:22])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][CH2:8][C:9]([F:21])([F:20])[C:10]([F:19])([F:18])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5].CN[N:41]([CH2:44][CH2:45][CH3:46])NC.C(=O)([O-])[O-].[K+].[K+].[C:53](OCC)(=O)C.[C:59](#[N:61])C>>[CH3:53][N:61]([CH2:46][CH2:45][CH2:44][NH:41][CH:2]([CH2:3][C:4]([O:6][CH2:7][CH2:8][C:9]([F:21])([F:20])[C:10]([F:18])([F:19])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5])[C:1]([O:23][CH2:24][CH2:25][C:26]([F:37])([F:38])[C:27]([F:35])([F:36])[C:28]([F:33])([F:34])[C:29]([F:32])([F:31])[F:30])=[O:22])[CH3:59]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 56982963N,N-dimethylaminopropylamineHCID 867598121,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) maleate

Produkt 1

HCID 87998872
1,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) 2-(3-(n,n-dimethylamino)propylamino)succinate
Ausbeute 75 %

Versuchsvorschrift

In an amount of 30.0 g (49 mmol) of 1,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) maleate, 6.8 mL (54 mmol) of N,N-dimethylaminopropylamine and 7.5 g (54 mmol) of potassium carbonate were dissolved in 120 mL of acetonitrile and refluxed for 6 hours with heating. Then, the reaction mixture was transferred to a separatory funnel and added with 1000 mL of ethyl acetate. The organic phase was washed with a saturated aqueous sodium hydrogencarbonate solution. Then, the organic layer was collected, and the organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:3 (volume ratio)) to obtain 2.64 g (yield: 75%) of the target compound as a brown oily compound.

Aufarbeitung

  1. temperaturerefluxed for 6 hours
  2. temperaturewith heating
  3. customThen, the reaction mixture was transferred to a separatory funnel
  4. washThe organic phase was washed with a saturated aqueous sodium hydrogencarbonate solution
  5. customThen, the organic layer was collected
  6. customthe organic solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:3 (volume ratio))

Quellen und Nachweise

ORD-Eintrag
ord-b6c10d57bf72403dabfc5134ff89c13f
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06747169B2

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