Pyridine → N-Methoxy-N-methylbutyramide

HRID 81838

Reaktionsgleichung

Reaktionsgleichung von HRID 81838
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[C:12](Cl)(=[O:16])[CH2:13][CH2:14][CH3:15]>C(Cl)Cl.O>[CH3:11][O:10][N:9]([CH3:8])[C:12](=[O:16])[CH2:13][CH2:14][CH3:15]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Produkt 1

HCID 13704543N-Methoxy-N-methylbutyramideAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridine (100 mL) was cooled to 0° C., and N,O-dimethylhydroxylamine hydrochloride (20.14 g, 206 mmol) was added with stirring. This solution was stirred for 10 minutes, and then a solution of butyryl chloride (19.5 ml, 20 g, 188 mmol) dissolved in 50 ml methylene chloride was added via addition funnel over 30 minutes. A precipitate formed after 5 minutes. This suspension was stirred and allowed to warm to room temperature. Stirring was continued for 2.0 hours, and the reaction was diluted with water, extracted with methylene chloride twice. The methylene chloride layers were combined and washed with 1 N HCl twice and once with brine. Diethyl ether (100 mL) was added to facilitate emulsion separation, and the organic layer was separated and washed with saturated bicarbonate solution, brine, and dried over magnesium sulfate. The solution was filtered and the solvent removed in vacuo to give N-Methoxy-N-methyl-butyramide as an oil (22.1 g, 89%).

Aufarbeitung

  1. stirringThis solution was stirred for 10 minutes
  2. additionwas added via addition funnel over 30 minutes
  3. customA precipitate formed after 5 minutes
  4. stirringThis suspension was stirred
  5. stirringStirring
  6. extractionextracted with methylene chloride twice
  7. washwashed with 1 N HCl twice
  8. additionDiethyl ether (100 mL) was added
  9. customemulsion separation
  10. customthe organic layer was separated
  11. washwashed with saturated bicarbonate solution, brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationThe solution was filtered
  14. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4e2ee6e098864000b4f5366db6ece7ce
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846705B2

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