Aniline → Acetamide, 2-cyano-N-phenyl-

HRID 599504

Reaktionsgleichung

Reaktionsgleichung von HRID 599504
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[C:1]([CH2:3][C:4]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:6])#[N:2]

Komponenten

6

Edukt 4

HCID 6115AnilineHCID 9740Cyanoacetic acidHCID 10340Sodium CarbonateHCID 24819Phosphorus pentachloride

Produkt 1

HCID 69296Acetamide, 2-cyano-N-phenyl-Ausbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Cyanoacetic acid (1.0 g, 11.7 mmol) is added to a stirred suspension of PCl5 (2.4 g, 11.7 mmol) in dry dichloromethane (200 ml). The reaction mixture is heated to reflux and kept stirring for 30 min. After cooling to rt, aniline (1.07 ml, 11.7 mmol) is added dropwise and the reaction is stirred at reflux for additional 2 h, then cooled to 0° C. and neutralized by addition of aqueous saturated Na2CO3 solution. The precipitate is filtered off, washed with water and dried under high vacuum to give title compound (1.54 g) as a white solid in 82% yield: tR (LC-2) 1.50 min; ESI-MS(+): m/z 183.33 [M+Na]+ (calcd 160.17 for C9H8N2O).

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. stirringthe reaction is stirred
  4. temperatureat reflux for additional 2 h
  5. temperaturecooled to 0° C.
  6. filtrationThe precipitate is filtered off
  7. washwashed with water
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-beb61a672d1945c693a4116135063da8
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897788B2

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