Ethyl Acetate → [5-Acetyl-3-(tert-butyl)-2-methoxyanilino]methyl cyanide

HRID 1295970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295970
Br[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].[NH2:11][C:12]1[CH:13]=[C:14]([C:24](=[O:26])[CH3:25])[CH:15]=[C:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]=1[O:18][CH3:19].C(OCC)(=O)C>CN(C)C=O>[C:24]([C:14]1[CH:15]=[C:16]([C:20]([CH3:21])([CH3:22])[CH3:23])[C:17]([O:18][CH3:19])=[C:12]([CH:13]=1)[NH:11][CH2:2][C:3]#[N:4])(=[O:26])[CH3:25]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 22929815HCID 22929815, Verbindung

Produkt 1

HCID 22930120[5-Acetyl-3-(tert-butyl)-2-methoxyanilino]methyl cyanide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Bromoacetonitrile (6 ml) and potassium carbonate (1.4 g) were added to a solution of 1-[3-amino-5-(tert-butyl)-4-methoxyphenyl]-1-ethanone (2.0 g, 9.0 mmol) in dimethylformamide (50 ml) and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, ethyl acetate was added, washed was performed with water and brine in that order, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (3.2 g) as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c8d4d4db58d648f1beba4163cba6303f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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