Acetonitrile → 4-(Heptafluoropropylthio)aniline

HRID 713605

Reaktionsgleichung

Reaktionsgleichung von HRID 713605
C(#N)C.[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.I[C:20]([F:29])([F:28])[C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23]>CCOCC>[F:26][C:21]([F:27])([C:22]([F:25])([F:24])[F:23])[C:20]([F:29])([F:28])[S:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 145104-AminothiophenolHCID 33977Perfluoropropyl iodide

Produkt 1

HCID 20526094-(Heptafluoropropylthio)anilineAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 20 ml of an acetonitrile solution of 1.25 g of 4-aminothiophenol and 1.11 g of triethylamine, 5.91 g of 1-iodoheptafluoro-n-propane was added, and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with ether, washed with an aqueous solution of 1N sodium hydroxide and purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 1.85 g (yield 63%) of the title compound.

Aufarbeitung

  1. washwashed with an aqueous solution of 1N sodium hydroxide
  2. custompurified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-12edce81bf1c48a9a3e6e0185d7cafb0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09185912B2

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