Hexane → HCID 70816656, Verbindung

HRID 1887789

Reaktionsgleichung

Reaktionsgleichung von HRID 1887789
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.Cl[C:20](=[O:25])[C:21]([O:23][CH3:24])=[O:22].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[C:20]([N:12]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[C:8](=[O:11])[CH2:9][CH3:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:25]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 79846Methyl chloroglyoxylateHCID 708166141-(4-Chloro-2-phenylamino-phenyl)-propan-1-one

Produkt 1

HCID 70816656HCID 70816656, VerbindungAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 1-(4-chloro-2-phenylamino-phenyl)-propan-1-one (13.0 g, 50.2 mmol) in toluene (150 mL) was added methyl chlorooxoacetate (42.86 g, 350.0 mmol) at room temperature under nitrogen. The reaction mixture was heated at reflux at 110° C. for 16 hr. Completion of the reaction was monitored by silica TLC (mobile phase; hexane:ethyl acetate=1:1; Rf=0.5). The reaction mixture was concentrated under vacuum to afford 15.2 g (87.6% crude yield) of N-(5-chloro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester. The crude product was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d8fb32f5730d4ecaa7e2e137302bf31b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501732B2

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