1,1-Bis(methylthio)-2-nitroethylene → N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamine

HRID 1043518

Reaktionsgleichung

Reaktionsgleichung von HRID 1043518
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[N+:12]([CH:15]=[C:16](SC)[S:17][CH3:18])([O-:14])=[O:13]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][CH3:11])[C:16]([S:17][CH3:18])=[CH:15][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 11137568N-((6-Chloropyridin-3-yl)methyl)ethanamine

Produkt 1

HCID 54422628N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamineAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 100 ml three necked round bottom flask was added N-((6-chloropyridin-3-yl)methyl)ethanamine (17.0 g, 0.1 mol), (2-nitroethene-1,1-diyl)bis(methylsulfane) (15.0 g, 0.09 mol), dry ethanol (50 mL). The mixture was refluxed. After completion, the reaction mixture was cooled to r.t. and concentrated under reduced pressure to obtain crude product as oil, which was purified by column chromatography to afford 5.3 g N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1-(methylthio)-2-nitroethenamine in 18.5% yield.

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. concentrationconcentrated under reduced pressure
  3. customto obtain crude product as oil, which
  4. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9199bef9f13a44e7aa1e2e26d175dd72
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563546B2

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