Hydrochloric Acid → 3-(4-Acetoxybutylsulfanyl)benzonitrile

HRID 1985832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1985832
[SH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].[C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23]Br)(=[O:18])[CH3:17].Cl>CN(C)C=O>[C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][S:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6])(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 147953343-Sulfanylbenzonitrile

Produkt 1

HCID 231438643-(4-Acetoxybutylsulfanyl)benzonitrileAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Mercaptobenzonitrile (0.40 g) and potassium carbonate (0.61 g) were suspended in N,N-dimethylformamide (5 mL). To the reaction mixture was added 4-bromobutyl acetate (0.63 g), and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5) to give the title compound (0.75 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-9fc4035c755f400581a7ab026b125eb2
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547680B2

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