3-(Chloromethyl)pyridine → 3-(3-Pyridylmethyl)2-nitromethylenethiazolidine

HRID 231172

Reaktionsgleichung

Reaktionsgleichung von HRID 231172
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].[H-].[Na+].[H][H].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Cl)[CH:15]=1>C(#N)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:9]2[CH2:8][CH2:7][S:6][C:5]2=[CH:4][N+:1]([O-:3])=[O:2])[CH:15]=1

Komponenten

6

Edukt 4

HCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 38355832-Nitromethylene-thiazolidineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 542512073-(3-Pyridylmethyl)2-nitromethylenethiazolidineAusbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

2-Nitromethylenethiazolidine (2.9 g) was suspended in dry acetonitrile (30 ml), and 60% sodium hydride (0.9 g) was added under a nitrogen stream. Then, the mixture was stirred at room temperature until the generation of hydrogen ceased. A solution of 3-picolyl chloride (3.2 g) in dry acetonitrile (5 ml) was added, and the mixture was stirred at room temperature for 3 hours. Acetonitrile was distilled off under reduced pressure. Dichloromethane was added to the residue, and the mixture was washed with water. Dichloromethane was then distilled off from the dichloromethane layer. The remaining oily product was purified by column chromatography to give the desired 3-(3-pyridylmethyl)2-nitromethylenethiazolidine (0.5 g).

Aufarbeitung

  1. distillationAcetonitrile was distilled off under reduced pressure
  2. additionDichloromethane was added to the residue
  3. washthe mixture was washed with water
  4. distillationDichloromethane was then distilled off from the dichloromethane layer
  5. customThe remaining oily product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2c9768b86e0a44aeabf6cfeff8924499
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845106

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