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

HRID 2211052Notes

Reaction equation

HRID 2211052 reaction equation
[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]

Participants

6

Reactant 5

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

Product 1

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

Procedure

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. nD22 1.5880

Workup

  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

Sources & evidence

ORD record
ord-2151f57618094ceab8912909d5b84a56
Source dataset
uspto-grants-1995_10
Patent number
US05461167

Reaction notes

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