Water → HCID 52911165, compound

HRID 1425962Notes

Reaction equation

HRID 1425962 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1.[CH2:15]([O:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16].O>CS(C)=O.C(OCC)(=O)C>[CH2:15]([O:17][C:18](=[O:25])[CH:19]([C:11]1[N:10]=[N:9][C:8]([Cl:7])=[CH:13][CH:12]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 673313,6-Dichloropyridazine

Product 1

HCID 52911165HCID 52911165, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Cesium carbonate (43.7 g) was added to a solution of 3,6-dichloropyridazine (10.0 g) and malonic acid diethyl ester (15.2 mL) in dimethyl sulfoxide (20 mL) at room temperature. The mixture was stirred at 110° C. for 1 h and then cooled to room temperature. Water and ethyl acetate were added and the resulting mixture was filtered over Celite. The aqueous phase of the filtrate was separated and extracted twice with ethyl acetate. The extracts and the organic phase of the filtrate were combined and washed with water and brine. Silica gel (50 g) and charcoal (5 g) were then added and the resulting mixture was stirred for 30 min at room temperature. The silica gel and charcoal were separated by filtration and the filtrate was concentrated to give the crude title compound that was used without further purification. Yield: 19.0 g (ca. 65% pure); LC (method 1): tR=1.25 min; Mass spectrum (ESI+): m/z=273/275 (Cl) [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe resulting mixture was filtered over Celite
  3. customThe aqueous phase of the filtrate was separated
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water and brine
  6. additionSilica gel (50 g) and charcoal (5 g) were then added
  7. stirringthe resulting mixture was stirred for 30 min at room temperature
  8. customThe silica gel and charcoal were separated by filtration
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a9be77474b6543d8a5923465c6ec4db7
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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