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Triethylamine → HCID 20431439, Verbindung

HRID 1708858
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1708858
[CH:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH2:2].ClCC=CC1C=CC=CC=1.C(N(CC)CC)C.[F:28][C:29]([F:48])([C:33]([F:47])([F:46])[C:34]([F:45])([F:44])[C:35]([F:43])([F:42])[C:36]([F:41])([F:40])[CH:37]([F:39])[F:38])[C:30](Cl)=[O:31]>C(C1C=CC=C(C(C)(C)C)C=1O)(C)(C)C.C(#N)C>[CH:1]([N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:30](=[O:31])[C:29]([F:28])([F:48])[C:33]([F:46])([F:47])[C:34]([F:44])([F:45])[C:35]([F:42])([F:43])[C:36]([F:40])([F:41])[CH:37]([F:38])[F:39])=[CH2:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 27761327H-Perfluoroheptanoyl chlorideHCID 13751050Vinylbenzylamine

Produkt 1

HCID 20431439HCID 20431439, VerbindungAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 31405
2,6-Di-tert-butylphenol
Katalysator
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

300 ml of acetonitrile, 33.9 g (0.3 mol) of vinylbenzylamine (synthesized by the method described in "Kobunshi Gakkai Yokoshu", vol. 26, page 834 (G3 C-07) (1977) from chloromethylstyrene (meta:para=about 6:4); p.b.: 82° C./1.5 mm Hg), 30.3 g (0.3 mol) of triethylamine, and 0.5 g of 2,6-di-t-butylphenol were charged into a 500-ml three-necked flask equipped with a stirrer, and a calcium chloride tube, and the mixture was then cooled with ice water. 109.5 g (0.3 mol) of the 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-n-heptanoic acid chloride synthesized in Synthesis Example 1 was added dropwise, with stirring and ice-cooling. Next, the mixture was stirred for 1 hour at room temperature, and the deposited triethylamine hydrochloride was filtered off. The filtrate was distilled under reduced pressure to remove the acetonitrile, 200 ml of ethyl acetate was added to the remainder to be dissolved, and white insolubles were filtered off. The filtrate was distilled under reduced pressure to be condensed, and 300 ml of n-hexane was added to the remainder, followed by cooling. The deposited white crystals were filtered and dried in vacuo at room temperature, thus producing 90.1 g (yield: 65.2%; m.p.: 53° to 57° C.) of 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-n-heptanoic acid vinylbenzylamide.

Aufarbeitung

  1. customequipped with a stirrer, and a calcium chloride tube
  2. additionwas added dropwise
  3. temperatureice-cooling
  4. stirringNext, the mixture was stirred for 1 hour at room temperature
  5. filtrationthe deposited triethylamine hydrochloride was filtered off
  6. distillationThe filtrate was distilled under reduced pressure
  7. customto remove the acetonitrile, 200 ml of ethyl acetate
  8. additionwas added to the remainder
  9. dissolutionto be dissolved
  10. filtrationwhite insolubles were filtered off
  11. distillationThe filtrate was distilled under reduced pressure
  12. customcondensed, and 300 ml of n-hexane
  13. additionwas added to the remainder
  14. temperatureby cooling
  15. filtrationThe deposited white crystals were filtered
  16. customdried in vacuo at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-f18de4123dd44e3ba715bad631854ee5
Quelldatensatz
uspto-grants-1990_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04946771

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