Water → 2-(2-Phenyl-ethen-1-yl)-3-difluoromethoxy-thiophene-2-carboxanilide

HRID 2084439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2084439
[C:1]1([CH:7]=[CH:8]C2C=CC=CC=2N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18]([CH2:21][CH3:22])CC)C.[F:23][CH:24]([F:34])[O:25][C:26]1[CH:30]=[CH:29][S:28][C:27]=1[C:31](Cl)=[O:32].O>C1(C)C=CC=CC=1>[C:1]1([CH:7]=[CH:8][C:27]2([C:31]([NH:18][C:21]3[CH:22]=[CH:3][CH:2]=[CH:1][CH:6]=3)=[O:32])[CH:26]([O:25][CH:24]([F:34])[F:23])[CH:30]=[CH:29][S:28]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 139378AminostilbeneHCID 111275992-Thiophenecarbonyl chloride, 3-(difluoromethoxy)-

Produkt 1

HCID 698864132-(2-Phenyl-ethen-1-yl)-3-difluoromethoxy-thiophene-2-carboxanilideAusbeute 189,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

At room temperature, a solution of 0.3 g (0.0015 mol) of 2-(2-phenyl-ethen-1-yl)-aniline in 2 ml of toluene is admixed with a solution of 0.15 g (0.0015 mol) of triethylamine in 10 ml of toluene. At room temperature, 0.33 g (0.0015 mol) of 3-difluoromethoxy-thiophene-2-carbonyl chloride are added to this mixture with stirring. The mixture is subsequently heated to 50° C. and stirred at this temperature for 2 hours. For work-up, the reaction mixture is then cooled to room temperature and admixed with water. The organic phase is separated off, dried over sodium sulphate and then concentrated under reduced pressure at 60° C. The residue that remains is chromatographed over silica gel using diethyl ether. Concentration of the eluate gives 0.53 g (95% of theory) of 2-(2-phenyl-ethen-1-yl)-3-difluoromethoxy-thiophene-2-carboxanilide in the form of a solid substance of melting point 80 to 82° C.

Aufarbeitung

  1. customAt room temperature
  2. stirringstirred at this temperature for 2 hours
  3. temperatureFor work-up, the reaction mixture is then cooled to room temperature
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure at 60° C
  7. customThe residue that remains is chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-466a20b292a147539ef12143e6d3d7fe
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716881B2

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