Benzyl Bromide → 6-Chloro-2-(phenylmethyl)-3(2H)-pyridazinone

HRID 2357927Notes

Reaction equation

HRID 2357927 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>COCCOC>[CH2:15]([N:6]1[C:5](=[O:8])[CH:4]=[CH:3][C:2]([Cl:1])=[N:7]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 2528286-Chloropyridazin-3-ol

Product 1

HCID 529031276-Chloro-2-(phenylmethyl)-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6-chloro-2H-pyridazine-3-one (3.50 g) was dissolved in DME (130 mL). To this solution, cesium carbonate (17.5 g) was added and the mixture was stirred at room temperature for 15 min in an argon atmosphere. Subsequently, benzyl bromide (4.00 mL) was added and the mixture was stirred at room temperature for 3.5 hours. The insoluble inorganic residue was removed by filtration and the filtrate was concentrated. Water was then added to the residue and the mixture was extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the resulting crystals were recrystallized from ethyl acetate/petroleum ether to afford the title compound as a pale yellow powder (4.94 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 3.5 hours
  2. customThe insoluble inorganic residue was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionWater was then added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting crystals were recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-06e9bc60625e427ead564be4498a36ed
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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