Dimethyl Sulfoxide → HCID 57454888, compound

HRID 1907684Notes

Reaction equation

HRID 1907684 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([CH3:19])[CH:3]=1.CS(C)=O.[Cl-].[Na+]>O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([CH3:19])[CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 57950227HCID 57950227, compound

Product 1

HCID 57454888HCID 57454888, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
137.5 °C

Procedure

1.81 g of diethyl (6-chloro-4-methyl-3-pyridazinyl)malonate and 15 ml of dimethyl sulfoxide were mixed. To the mixture was added 0.45 g of sodium chloride and 0.23 g of water. The mixture was stirred for about 40 minutes at an inner temperature of 125 to 150° 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. 1.05 g of the resultant residue was subjected to silica gel column chromatography, to obtain 0.91 g of ethyl (6-chloro-4-methyl-3-pyridazinyl)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-97fd59f826804c26bab8e3fc1515ca42
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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