Water → HCID 68760855, Verbindung

HRID 494389

Reaktionsgleichung

Reaktionsgleichung von HRID 494389
[H-].[Na+].[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Cl[C:16]1[CH:17]=[CH:18][C:19]([N+:27]([O-:29])=[O:28])=[C:20]([CH:26]=1)[C:21]([N:23]([CH3:25])[CH3:24])=[O:22].O>CN(C)C=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:16]1[CH:17]=[CH:18][C:19]([N+:27]([O-:29])=[O:28])=[C:20]([C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[CH:26]=1)[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2733872tert-Butyl methyl malonateHCID 229348075-Chloro-N,N-dimethyl-2-nitrobenzamide

Produkt 1

HCID 68760855HCID 68760855, VerbindungAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (350 mg) was dissolved in dimethylformamide (10 mL)), and the solution was cooled to 0° C. After addition of tert-butyl methyl malonate (1.52 g), the mixture was stirred for one hour, and the 5-chloro-N,N-dimethyl-2-nitrobenzamide (1.0 g) obtained in Example 2a) was added thereto. The mixture was stirred at 70° C. for 4.5 hours and water was added thereto. The resulting solution was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and purified by column chromatography on silica gel with ethyl acetate:hexane=1:1 to give the title compound (1.29 g).

Aufarbeitung

  1. stirringThe mixture was stirred at 70° C. for 4.5 hours
  2. concentrationThe resulting solution was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. custompurified by column chromatography on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e35f076fe60b47d98db6c6cc01f6b664
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538140B2

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