Methyl iodide → HCID 69962996, compound

HRID 1291317Notes

Reaction equation

HRID 1291317 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:17]4[C:18](=[O:23])[NH:19][N:20]=[C:21]([Cl:22])[C:16]=4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][N:13]3[C:17]4[C:18](=[O:23])[N:19]([CH3:28])[N:20]=[C:21]([Cl:22])[C:16]=4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18919091HCID 18919091, compound

Product 1

HCID 69962996HCID 69962996, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (200 ml) was dissolved 1-[4-(4-chlorobenzoyl)benzyl]-4-chloropyrrolo [2,3-d]pyridazin-7(6H)-one (830 mg) followed by addition of potassium carbonate (2.11 g). Then, methyl iodide (0.13 ml) was added and the mixture was stirred at room temperature for 95 hours. This reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (200 ml). The organic layer was washed with water (100 ml) 3 times and further with saturated aqueous NaCl solution (100 ml) and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure and the resulting crystals were rinsed with ethyl acetate to provide 742 mg (yield 84%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (200 ml)
  2. washThe organic layer was washed with water (100 ml) 3 times and further with saturated aqueous NaCl solution (100 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. washthe resulting crystals were rinsed with ethyl acetate

Sources & evidence

ORD record
ord-8f0ffa0db2df46ae97ffa91300eab3d3
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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