Dimethylformamide → 1-Benzyl-7-chloro-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one
Reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.CN(C)C=O.[CH2:14]([N:21]1[C:25]2[C:26]([Cl:31])=[N:27][NH:28][C:29](=O)[C:24]=2[N:23]=[CH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C(OCC)(=O)C>[CH2:14]([N:21]1[C:25]2[C:26]([Cl:31])=[N:27][N:28]([CH3:29])[C:1](=[O:4])[C:24]=2[N:23]=[CH:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
0.604 g of potassium carbonate and 0.297 ml of methyl iodide were added to a 30 ml N,N-dimethylformamide solution of 1.035 g of 1-benzyl-7-chloro-1,5-dihydroimidazo[4,5-d]pyridazin-4-one (J. A. Carbon Journal of the American Chemical Society, 80, pp. 6083, 1958), and the mixture was stirred at room temperature for 15 hours. 300 ml of ethyl acetate and 100 ml of water were added to the solution, and the organic layer was washed twice with 100 ml of water and then with 100 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.280 g of the title compound was obtained from the fraction eluted with ethyl acetate.
Workup
- washthe organic layer was washed twice with 100 ml of water
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9c0c6ae43fd34ef1b22b194146871b42
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772226B2
Reaction notes
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