Water → HCID 54082816, compound

HRID 1608654Notes

Reaction equation

HRID 1608654 reaction equation
[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[C:16]1([CH:22]=[CH:23][CH2:24]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[Cl:1][C:2]1[C:3](=[O:9])[N:4]([CH2:24][CH:23]=[CH:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 732474,5-Dichloro-3-hydroxypyridazineHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 54082816HCID 54082816, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 16.5 g (100 mmoles) of 4,5-dichloro-3(2H)-pyridazinone and 150 g (163 mmoles) of anhydrous potassium carbonate in 100 ml of anhydrous dimethylformamide a solution of 16.8 g (110 mmoles) of 3-phenyl-2-propenyl chloride in 5 ml of anhydrous dimethylformamide is dropped under stirring and cooling at a temperature below 15° C. The reaction mixture is stirred at room temperature for a day and poured onto 600 ml of water under stirring. The separated crystals are filtered, washed with water, dried and optionally purified by treating with aluminium oxide in a benzene solution. Thus 24.9 g (89%) of the desired compound are obtained. M.p.: 98°-99° C.

Workup

  1. additionis dropped
  2. temperaturecooling at a temperature below 15° C
  3. stirringThe reaction mixture is stirred at room temperature for a day
  4. stirringunder stirring
  5. filtrationThe separated crystals are filtered
  6. washwashed with water
  7. customdried
  8. customoptionally purified
  9. additionby treating with aluminium oxide in a benzene solution

Sources & evidence

ORD record
ord-94c237d740444429ba2471ca92352427
Source dataset
uspto-grants-1995_03
Patent number
US05395934

Reaction notes

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