Ethyl Acetate → tert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamate

HRID 1861962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861962
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].[C-:18]#[N:19].[Na+].C(OCC)(=O)C>CS(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:18]#[N:19])=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22981310HCID 22981310, Verbindung

Produkt 1

HCID 53943733tert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamateAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The compound (155.1 mg) obtained in Example 519 was dissolved in dimethyl sulfoxide (5 ml). To the solution, sodium cyanide (127 mg) was added and the mixture was heated at 50° C. under stirring for 10 min. To the resulting reaction mixture, ethyl acetate was added and the organic layer was washed with water twice, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 77.7 mg of the titled compound (yield, 61%).

Aufarbeitung

  1. additionwas added
  2. washthe organic layer was washed with water twice
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0e2092eb16e741319a97bb91a82ba399
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534546B1

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