Methanol → Pyridine, 2-(methylthio)-3-nitro-

HRID 22881

Reaktionsgleichung

Reaktionsgleichung von HRID 22881
CO.Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:13][S-:14].[Na+]>O>[CH3:13][S:14][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1

Komponenten

5

Edukt 3

HCID 887Methanol2×HCID 796132-Chloro-3-nitropyridineHCID 4378561Sodium methanethiolate

Produkt 1

HCID 572042Pyridine, 2-(methylthio)-3-nitro-Ausbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A methanol (50 ml) solution of 2-chloro-3-nitropyridine (4.30 g, 27.1 mmol) was added dropwise to a methanol (30 ml) solution of sodium thiomethoxide (2.10 g, 28.5 mmol) while being cooled with ice, and the mixed solution was stirred for 17 hours. Water was then added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crystals were recrystallized from a mixture of an ethyl acetate-hexane mixture to obtain 2.93 g (yield 64%) of 2-methylthio-3-nitropyridine as a yellow needle crystal.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. distillationSubsequently, the solvent was distilled off
  6. customthe resulting crystals were recrystallized from a mixture of an ethyl acetate-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-7257ee8926b142a19f5f9af085d27b45
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849647B1

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