Dimethyl Sulfoxide → Ethyl 3,5-dichloro-2-pyridineacetate

HRID 1907680Notes

Reaction equation

HRID 1907680 reaction equation
[Cl:1][C:2]1[C:3]([CH:9](C(OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CS(C)=O.[Cl-].[Na+]>O>[Cl:1][C:2]1[C:3]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 57950225HCID 57950225, compound

Product 1

HCID 57447457Ethyl 3,5-dichloro-2-pyridineacetateYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
142.5 °C

Procedure

6.75 g of diethyl (3,5-dichloro-2-pyridyl)malonate and 20 ml of dimethyl sulfoxide were mixed. To the mixture was added 1.57 g of sodium chloride and 0.79 g of water. The mixture was stirred for about 40 minutes at an inner temperature of 135 to 150° C. The mixture was allowed to cool to room temperature, then, water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure, to obtain 4.76 g of ethyl (3,5-dichloro-2-pyridyl)acetate.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab465b48078649a28e56d38576c31186
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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