Water → 6-(2,6-Diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester

HRID 251632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251632
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10](Cl)=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])[CH3:2].[CH3:24][S-:25].[Na+].O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10]([S:25][CH3:24])=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 59678345Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

Produkt 1

HCID 669940156-(2,6-Diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester (200 mg, 0.60 mmol) and sodium thiomethoxide (126 mg, 1.80 mmol) in DMF (5 mL) is heated at 70° C. overnight. After cooling, water (20 mL) is added and the resulting mixture is extracted with EtOAc. The combined extracts are washed with brine, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel to give 6-(2,6-diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe resulting mixture is extracted with EtOAc
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f4ca2c609e354f30816926c5c1d97730
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863454B2

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