Water → 2,3-Dichloro-1-[4-(2,4-dichlorobenzoyl)benzyl]-5-methyl-1H-pyrrolo [2,3-d]pyridazin-4(5H)-one
Reaction equation
[Cl:1][C:2]1[NH:12][C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[C:3]=1[Cl:13].[H-].[Na+].[Cl:16][C:17]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:18]=1[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)=[O:20].O>CN(C=O)C>[Cl:1][C:2]1[N:12]([CH2:25][C:24]2[CH:23]=[CH:22][C:21]([C:19](=[O:20])[C:18]3[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:17]=3[Cl:16])=[CH:28][CH:27]=2)[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[C:3]=1[Cl:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,3-dichloro-5-methyl-1H-pyrrolo [2,3-d]pyridazin-4(5H)-one (404 mg) in DMF (70 ml) was dripped into a suspension of 60% sodium hydride-oil (96 mg) in DMF (10 ml) on an ice-water bath. The mixture was stirred at room temperature for 2 hours, after which a solution of 4-(2,4-dichlorobenzoyl)benzyl bromide (757 mg) in DMF (15 ml) was added and the mixture was further stirred at room temperature for 16 hours. The reaction was stopped by adding water and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with ether to provide the title compound as yellowish brown powder (471 mg, yield 49%).
Workup
- stirringthe mixture was further stirred at room temperature for 16 hours
- extractionthe reaction mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- washThe residue was washed with ether
Sources & evidence
- ORD record
- ord-5dbf934e958b495a93c791864fcdaa66
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753664
Reaction notes
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