Acetyl chloride → N-Acetyl-2-chloro-3-oxobutyramide

HRID 2057962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057962
[Cl:1][CH:2]([C:6](=[O:8])[CH3:7])[C:3]([NH2:5])=[O:4].[C:9](Cl)(=[O:11])[CH3:10]>C(OC(=O)C)(=O)C>[C:9]([NH:5][C:3](=[O:4])[CH:2]([Cl:1])[C:6](=[O:8])[CH3:7])(=[O:11])[CH3:10]

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 3017751Butanamide, 2-chloro-3-oxo-

Produkt 1

HCID 20295024N-Acetyl-2-chloro-3-oxobutyramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-3-oxobutyramide (1 g) in acetic anhydride (5 ml) containing acetyl chloride (1 ml) was heated in a 100° oil bath for 2 hours. Excess reagent was evaporated under reduced pressure and the residue was vacuum distilled in a kugelrohr apparatus. The distilled product crystallized to give a colorless solid with mp 54°-8°; ir (Nujol) 3200 and 1700 cm-1 (broad); nmr (CDCl2) 2.28 (CH3), 2.47 (CH3), 5.53 (CH), and 9.7 ppm (NH), (a weaker set of singlets corresponding to the enol appears at 2.23, 2.52, and 8.7 ppm); mass spectrum m/e 43 (100%), 93, 135, and 177 (M+).

Aufarbeitung

  1. temperaturewas heated in a 100° oil bath for 2 hours
  2. customExcess reagent was evaporated under reduced pressure
  3. distillationdistilled in a kugelrohr apparatus
  4. customThe distilled product crystallized
  5. customto give a colorless solid with mp 54°-8°

Quellen und Nachweise

ORD-Eintrag
ord-fbea13275c504939a4b0ef9d09e448fb
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04214002

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