Diethyl Malonate → HCID 57950227, compound

HRID 1907683Notes

Reaction equation

HRID 1907683 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8].[C:10]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:9][C:5]1[N:4]=[N:3][C:2]([CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([CH3:8])[CH:6]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 879233,6-Dichloro-4-methylpyridazine

Product 1

HCID 57950227HCID 57950227, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4.29 g of 3,6-dichloro-4-methylpyridazine, 8.80 g of diethyl malonate, 25 ml of dimethyl sulfoxide and 17.9 g of cesium carbonate was stirred for 4 hours at 110° C. under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, then, to this was added ice 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. 7.08 g of the resultant residue was subjected to silica gel column chromatography, to obtain 1.95 g of diethyl (6-chloro-4-methyl-3-pyridazinyl)malonate.

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-38a3d4e79ccd459f9898b882a0f5505b
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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