Dimethylformamide → 2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one

HRID 1865829Notes

Reaction equation

HRID 1865829 reaction equation
[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Cl:8].CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH2:21]([N:4]1[C:3](=[O:9])[C:2]([Cl:1])=[C:7]([Cl:8])[CH:6]=[N:5]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 732474,5-Dichloro-3-hydroxypyridazine

Product 1

HCID 7224382-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-oneYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask was added 4,5-dichloropyridazin-3(2H)-one (50 gm, 303.03 mmol), DMF (150 ml), K2CO3 (46 gm, 333.33) and benzyl bromide (51.83 gm, 303.03 mmol). The reaction was stirred at rt for 16 hrs. After this time, the reaction mixture was slowly poured into water (500 ml) and a solid precipitate formed. The slurry was stirred at rt for 1 hr. After this time, the reaction mixture was filtered and the solid was collected. The solid was dried under vacuum to give product 2-benzyl-4,5-dichloropyridazin-3(2H)-one as tan-colored solid (74 gm, 97% yield). HPLC retention time (method A)2.788 min; LCMS (M+1)=255.1.

Workup

  1. customa solid precipitate formed
  2. stirringThe slurry was stirred at rt for 1 hr
  3. filtrationAfter this time, the reaction mixture was filtered
  4. customthe solid was collected
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-f1e5df4715e84669aa907159f5cace7c
Source dataset
uspto-grants-2009_12
Patent number
US07629342B2

Reaction notes

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