Dimethyl Sulfoxide → HCID 57447458, compound

HRID 1907686Notes

Reaction equation

HRID 1907686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.CS(C)=O.[Cl-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 57950226HCID 57950226, compound

Product 1

HCID 57447458HCID 57447458, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
138.5 °C

Procedure

5.83 g of diethyl (5-chloro-3-fluoro-2-pyridyl)malonate and 25 ml of dimethyl sulfoxide were mixed. To the mixture were added 1.29 g of sodium chloride and 0.72 g of water. The mixture was stirred for about 40 minutes at an inner temperature of 135 to 142° C. The reaction mixture was allowed to cool to room temperature, then, to the reaction mixture was added water, 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. 4.03 g of the resultant residue was subjected to silica gel column chromatography, to obtain 3.16 g of ethyl (5-chloro-3-fluoro-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-722999eb596c47f5ae00e14b61536786
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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