Hydrochloric Acid → 2,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamide

HRID 35022

Reaktionsgleichung

Reaktionsgleichung von HRID 35022
[F:1][C:2]([F:16])([C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:3]([OH:5])=O.C(OC#C)C.[NH2:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][C:28]#[N:29])=[CH:25][CH:24]=1.Cl>C(OCC)(=O)C>[F:16][C:2]([F:1])([C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:3]([NH:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][C:28]#[N:29])=[CH:25][CH:24]=1)=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 61239Ether, ethyl ethynylHCID 75921Perfluoropentanoic acidHCID 770004-Aminophenylacetonitrile

Produkt 1

HCID 142538082,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Perfluorovaleric acid (10 g), ethoxyacetylene (12.3 g) and ethyl acetate (175 mL) were stirred overnight at room temperature under a nitrogen atmosphere. 4-Aminobenzylcyanide (5.57 g) was added and the resulting mixture was allowed to stir at room temperature for 24 hours. The reaction mixture was cooled in ice and 10% aqueous HCl solution was added until a precipitate formed. The solid was collected and washed with water and hexane, sequentially, and dried in vacuo to yield 7.4 g (53%) of 2,2,3,3,4,4,5,5,5-nonafluoro-N-[4-(cyanomethyl)phenyl]pentanamide as a tan solid, m.p. 126°-128° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled in ice
  2. customformed
  3. customThe solid was collected
  4. washwashed with water and hexane
  5. customsequentially, and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2b749b3013a4f95b6d4602cc7baf859
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764623

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