Dimethyl Sulfoxide → HCID 57447455, compound

HRID 1907674Notes

Reaction equation

HRID 1907674 reaction equation
[Cl:1][C:2]1[C:3]([CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.CS(C)=O.[Cl-].[Na+]>O>[Cl:1][C:2]1[C:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 57950214HCID 57950214, compound

Product 1

HCID 57447455HCID 57447455, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
142.5 °C

Procedure

3.70 g of diethyl (3-chloro-2-pyridyl)malonate and 15 ml of dimethyl sulfoxide were mixed. To the mixture was added 0.95 g of sodium chloride and 0.49 g of water. The mixture was stirred for about 20 minutes at an inner temperature of 135 to 150° C. The reaction mixture was allowed to cool to room temperature, then, water was added to the reaction mixture, and extracted with ethyl acetate. After liquid separation, the organic layer was washed with saturated brine twice, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure to obtain 2.57 g of ethyl (3-chloro-2-pyridyl)acetate.

Workup

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

Sources & evidence

ORD record
ord-e583eaf9d39e433886d2aee269ca22f8
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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