Dimethylformamide dimethyl acetal → N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide

HRID 968200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968200
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([CH3:13])=[O:12])[CH:5]=1)=[O:3].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>C(OCC)(=O)C.CCOCC>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:1][C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:12])[CH3:13])[CH:7]=[CH:8][CH:9]=1)=[O:3]

Komponenten

5

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 3462023'-Acetamidoacetophenone

Produkt 1

HCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-acetamidoacetophenone 7 (20 g, 112.9 mmol), dimethylformamide dimethyl acetal (40.3 g, 338.6 mmol) was refluxed under nitrogen for 1 hour. The reaction mixture was cooled, diluted with ethyl acetate (150 mL) and ether (150 mL). The solid was collected by filtration, triturated with a solution of ethyl acetate and hexane (1:1, 200 mL). Compound 8 was obtained as a red-orange solid (23.6 g, 101.6 mmol, 90%). GC/MS, m/z=232 at tR=15.11 min (100%). LC/MS, [M+H]′=233.

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe solid was collected by filtration
  4. customtriturated with a solution of ethyl acetate and hexane (1:1, 200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-4658cafef4a24b5e87fc6808c8683331
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958342B2

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