Sodium Chloride → Methyl 4-[(2-ethoxy-1-methyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoate

HRID 1942494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942494
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[SH:22][CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[Na+]>CN(C)C=O>[CH2:27]([O:26][C:24](=[O:25])[CH:23]([S:22][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1)[CH3:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 519709Ethyl 2-mercaptopropionateHCID 10633188Methyl 4-chloro-2-methyl-5-nitrobenzoate

Produkt 1

HCID 67333305Methyl 4-[(2-ethoxy-1-methyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoateAusbeute 111,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 4-chloro-2-methyl-5-nitrobenzoate (2.52 g) in N,N-dimethylformamide (20 ml) were added potassium carbonate (3.04 g) and ethyl 2-mercaptopropionate (2.2 g), and the mixture was stirred at 80° C. for 4 hours. After the reaction was complete, to the mixture was added a saturated aqueous sodium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure to give methyl 4-[(2-ethoxy-1-methyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoate (4.0 g). Subsequently, the title compound was obtained in a similar manner to Reference Example 2.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e70aba7b41eb46e3be9735aa1df62a99
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389511B2

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