Sodium hydride → HCID 18412017, compound

HRID 992260Notes

Reaction equation

HRID 992260 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]([C:14](=O)[CH3:15])[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.[H-].[Na+].[Br:19][CH2:20][C:21](Cl)=[O:22]>O1CCCC1>[C:11]([C:10]1[C:14]([CH3:15])=[C:20]([Br:19])[C:21](=[O:22])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 89602Bromoacetyl chlorideHCID 178468337HCID 178468337, compound

Product 1

HCID 18412017HCID 18412017, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Pentan-2,3,4-trione 3-(4-chlorophenylhydrazone) (23.90 g) was added to a suspension of 66% sodium hydride (7.64 g) in anhydrous tetrahydrofuran (300 ml) under ice cooling, followed by stirring at room temperature for 30 minutes. Then, a solution of bromacetyl chloride (9.1 ml) in anhydrous tetrahydrofuran (100 ml) was added dropwise under ice cooling, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. After washing with water and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, the resulting residue was purified by silica gel column chromatography (acetone:hexane=1:9), and crystallized from hexane to obtain 6-acetyl-4-bromo-2-(4-chlorophenyl)-5-methyl-3(2H)-pyridazinone (11.96 g).

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe resulting residue was purified by silica gel column chromatography (acetone:hexane=1:9)
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-f128920b9185467e92e163542eabf163
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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