Allyl bromide → HCID 21406355, compound

HRID 972205Notes

Reaction equation

HRID 972205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CC(C)=O>[CH2:25]([O:8][C:7]1[C:6]([Cl:9])=[CH:5][C:4]([C:10]2[CH2:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:3][C:2]=1[Cl:1])[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 136409735HCID 136409735, compound

Product 1

HCID 21406355HCID 21406355, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 50 ml. of acetone was mixed 5 g. of 6-(3,5-dichloro-4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone obtained in Example 5 and 3.3 g. of anhydrous potassium carbonate and to the resulting mixture was added dropwise 2.4 g. of allyl bromide at room temperature while stirring. After completion of the addition, the mixture was heated under reflux for 4 hours. After cooling, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was recrystallized from ethanol to give 5.3 g. of the desired product of m.p. 137° C. (Yield 93%).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was recrystallized from ethanol
  8. customto give 5.3 g

Sources & evidence

ORD record
ord-4f0beae55e124702a35f894fd2d25a70
Source dataset
uspto-grants-1977_10
Patent number
US04052395

Reaction notes

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