1,1-Bis(methylthio)-2-nitroethylene → 1-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethylene

HRID 236266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236266
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].[CH3:15][S:16][C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20]>C(#N)C>[CH3:3][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]([S:16][CH3:15])=[CH:18][N+:19]([O-:21])=[O:20])[N:9]=1)[CH3:1]

Komponenten

4

Edukt 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Produkt 1

HCID 678972721-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethyleneAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

With 2 ml of acetonitrile were mixed 1 g of 2-{[2-(dimethylamino)methyl-4-thiazolyl]methylthio}ethylamine and 1.4 g of 1,1-bis(methylthio)-2-nitroethene, and the resulting mixture was subjected to reaction under reflux for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and 5 ml of ethanol was added to the resulting residue, after which the insolubles were removed by filtration. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:ethanol=20:1 by volume) to obtain 0.8 g (yield 53%) of oily 1-{2-[[2-(dimethylamino)methyl-4-thiazolyl]methylthio]ethylamino}-1-methylthio-2-nitroethene.

Aufarbeitung

  1. customthe resulting mixture was subjected to reaction
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure, and 5 ml of ethanol
  5. additionwas added to the resulting residue
  6. customafter which the insolubles were removed by filtration
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue thus obtained
  9. customwas purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:ethanol=20:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-52c8579f4eee4b8ea5835ef33b6e1536
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04643849

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