Dimethyl Sulfoxide → 1-Butyroyl-1-nitro-2,2-bis(methylthio)ethylene

HRID 377007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377007
[N+:1]([CH2:4][C:5](=[O:9])[CH2:6][CH2:7][CH3:8])([O-:3])=[O:2].[OH-].[Na+].[C:12](=S)=[S:13].CI.[CH3:17][S:18]([CH3:20])=O>>[C:5]([C:4]([N+:1]([O-:3])=[O:2])=[C:17]([S:13][CH3:12])[S:18][CH3:20])(=[O:9])[CH2:6][CH2:7][CH3:8]

Komponenten

6

Edukt 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 214474071-Nitropentan-2-one

Produkt 1

HCID 139210061-Butyroyl-1-nitro-2,2-bis(methylthio)ethylene

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 13.1 g of 1-nitro-2-pentanone in 200 ml of dimethylsulfoxide was added dropwise 44 g of 20% sodium hydroxide solution at 10-20° C. 12 g of carbon disulfide was then added dropwise to the solution at 10° C. and the mixture was stirred for 2 hours at 0-10° C. 57 g of methyliodide was dropped into the mixture with ice cooling and the reaction mixture was allowed to stand overnight at room temperature. This was then poured into ice water and the organic layer was extracted with dichloromethane. The extract was washed with water a few times, and after removing the solvent the residue was purified by chromatography on a silicagel column to give desired 1-butyroyl-1-nitro-2,2-bis (methylthio)ethylene. The yield is 3.0 g.

Aufarbeitung

  1. waitto stand overnight at room temperature
  2. extractionthe organic layer was extracted with dichloromethane
  3. washThe extract was washed with water a few times
  4. customafter removing the solvent the residue
  5. customwas purified by chromatography on a silicagel column

Quellen und Nachweise

ORD-Eintrag
ord-84a9aa9bdfc94040ab9bfdc4e476bcab
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022967

Notizen zur Reaktion

Wird geladen…