Sodium Azide → 4-Azidobutyrophenone

HRID 350843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350843
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[N-:13]=[N+:14]=[N-:15].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[N:13]([CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N+:14]=[N-:15]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 2535334-ChlorobutyrophenoneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 108779184-AzidobutyrophenoneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Chlorobutyrophenone (300.0 mg, 1.64 mmol) was dissolved in N,N-dimethylformamide (20 ml) at room tempaerature and then added to sodium azide (1.07 g, 16.42 mmol) at the same temperature, and thereafter stirred at 100° C. for 24 hours. The reaction solution was added to a saturated aqueous sodium hydrogencarbonate solution and then extracted by ethyl acetate, to obtain an organic layer. The extracted organic layer was washed with water and brine sequentially, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant saubstance was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1), whereby the target compound was obtained as a colorless oil (285.5 mg, 91.9%)

Aufarbeitung

  1. extractionextracted by ethyl acetate
  2. customto obtain an organic layer
  3. washThe extracted organic layer was washed with water and brine sequentially
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant saubstance was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1), whereby the target compound

Quellen und Nachweise

ORD-Eintrag
ord-5f1745edbc614bb18b61caa00673bf1c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183295B2

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