Dimethyl Sulfoxide → Ethyl nitroacetate

HRID 2351582Notes

Reaction equation

HRID 2351582 reaction equation
CS(C)=O.[H-].[Na+].[N+:7]([CH3:10])([O-:9])=[O:8].C([C:13]([O:15][CH2:16][CH3:17])=[O:14])#N>C(O)(=O)C>[N+:7]([CH2:10][C:13]([O:15][CH2:16][CH3:17])=[O:14])([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6375NitromethaneHCID 24758Sodium hydrideHCID 69336Ethyl cyanoformate

Product 1

HCID 69379Ethyl nitroacetateYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 100 ml three-neck round bottom flask, equipped with an addition funnel, a thermometer and a condenser topped with a nitrogen gas inlet tube, was added 20 ml of dimethylsulfoxide, 0.196 g (0.00815 mole) sodium hydride and then 0.5 g (0.00815 mole) of nitromethane was added dropwise at ambient temperature to give a slurry. 1.6 ml (0.0163 mole) of ethyl cyanoformate was then added dropwise forming a homogeneous solution and was then stirred for 2 hours at ambient temperature. The solution was made acidic by adding 30 ml of 1 Normal acetic acid with stirring. The product was extracted with ethyl acetate and dried over magnesium sulfate. Ethyl nitroacetate was formed in 83% yield as determined by gas chromatography.

Workup

  1. customTo a 100 ml three-neck round bottom flask, equipped with an addition funnel
  2. customa thermometer and a condenser topped with a nitrogen gas inlet tube
  3. customto give a slurry
  4. customforming a homogeneous solution
  5. stirringwith stirring
  6. extractionThe product was extracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-750a07285e284944abd356e41de81d6c
Source dataset
uspto-grants-1989_10
Patent number
US04873358

Reaction notes

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