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Acetonitrile → 2,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride

HRID 1180710
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1180710
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=O.P(Cl)(Cl)([Cl:18])=O.C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]=[C:3]([Cl:18])[C:2]([F:15])([F:14])[F:1])=[CH:7][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1012842,2,2-Trifluoro-N-(4-methoxy-phenyl)-acetamide

Produkt 1

HCID 104216822,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl ChlorideAusbeute 117,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857
Ethyl Acetate
Lösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

Ten grams (45.6 mmol) of 2,2,2-trifluoro-N-(4-methoxyphenyl)acetamide, 4.92 g (32.0 mmol) of phosphorus oxychloride, 9.23 g (91.2 mmol) of triethylamine, and 50 ml of acetonitrile were introduced into a 200 ml flask and reacted for 19 hours while being refluxed (82° C.). After the reaction, the reaction solution was cooled to room temperature, 30 ml of ethyl acetate was added thereto, and the precipitate was then filtered off. The filtrate was subjected to solvent removal by evaporation, and the crude product thus obtained was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7), resulting in 8.94 g of N-(4-methoxyphenyl)-2,2,2-trifluoroacetimidoyl chloride as a yellow liquid (yield: 82.5%).

Aufarbeitung

  1. customreacted for 19 hours
  2. customAfter the reaction
  3. temperaturethe reaction solution was cooled to room temperature
  4. filtrationthe precipitate was then filtered off
  5. customThe filtrate was subjected to solvent removal by evaporation
  6. customthe crude product thus obtained
  7. customwas purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)

Quellen und Nachweise

ORD-Eintrag
ord-351792d4ce63490185a24e459f14afb2
Quelldatensatz
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07282609B2

Notizen zur Reaktion

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