Benzonitrile, 4-(trifluoromethyl)- → HCID 178504795, Verbindung

HRID 1166348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166348
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C[Al](C)C.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:19]=[CH:20][C:21]([C:22](=[NH:23])[NH:9][C:8]2[CH:10]=[CH:11][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 796174-(Methylsulfonyl)anilineHCID 16682925Trimethylaluminum

Produkt 1

HCID 178504795HCID 178504795, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of 4-(methylsulfonyl)aniline (10 mmol) in toluene (100 mL), trimethylaluminum (2M solution in toluene, 15 mmol) is added over 15 minutes. The reaction mixture is warmed to room temperature and stirred for 2.5 hours. A solution of 4-trifluoromethylbenzonitrile (20 mmol) in toluene (50 mL) is added over 10 minutes and the reaction mixture is heated to 80-85° C. After 20 hours, the reaction mixture is cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue is washed with a mixture of methylene chloride/methanol (2/1). The combined filtrates are concentrated in vacuo and the resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL). The intermediate is filtered and washed with more of hexane/ether (2/1). The pale yellow solid 4-(trifluoromethyl)-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide is used in the next reaction without further purification.

Aufarbeitung

  1. additionis added over 15 minutes
  2. temperaturethe reaction mixture is heated to 80-85° C
  3. waitAfter 20 hours
  4. temperaturethe reaction mixture is cooled to room temperature
  5. filtrationAfter filtration
  6. washthe residue is washed with a mixture of methylene chloride/methanol (2/1)
  7. concentrationThe combined filtrates are concentrated in vacuo
  8. stirringthe resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL)
  9. filtrationThe intermediate is filtered
  10. washwashed with more of hexane/ether (2/1)
  11. customThe pale yellow solid 4-(trifluoromethyl)-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide is used in the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-1968365d91984f69a327468326313546
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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