Water → 4-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one

HRID 2390991

Reaktionsgleichung

Reaktionsgleichung von HRID 2390991
COC([C:5]1[C:9](=[O:10])[O:8][CH2:7][C:6]=1O)=O.[Cl:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][NH:20][CH3:21])=[CH:15][CH:14]=1.S([O-])(O)(=O)=O.[K+].O>C(#N)CCC.ClCCl>[Cl:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][N:20]([CH3:21])[C:6]2[CH2:7][O:8][C:9](=[O:10])[CH:5]=2)=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 54677706Methyl 4-hydroxy-2-oxo-2,5-dihydrofuran-3-carboxylate

Produkt 1

HCID 115504594-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-oneAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8008ButyronitrileLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a suspension of 18 g of 4-(methoxycarbonyl)-5-oxo-2,5-dihydrofuran-3-ol and 15 g of N-[(6-chloropyridin-3-yl)methyl]methylamine in 210 ml of butyronitrile are added, at room temperature, 16 g of potassium hydrogensulphate. The mixture is stirred at a temperature of 115° C. for 5 hours. Subsequently, the mixture is cooled to room temperature and admixed with 150 ml of water and 70 ml of dichloromethane. The organic phase is removed and the aqueous phase is extracted twice with 70 ml each time of methylene chloride. The combined organic phases are concentrated to dryness. 24 g of 4-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one are obtained in a purity of 88% (this corresponds to 92% yield).

Aufarbeitung

  1. additionare added, at room temperature
  2. temperatureSubsequently, the mixture is cooled to room temperature
  3. customThe organic phase is removed
  4. extractionthe aqueous phase is extracted twice with 70 ml each time of methylene chloride
  5. concentrationThe combined organic phases are concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e07d30df71024be7ad1cd76c8ef870c1
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273904B2

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