Chloromethyl Methyl Ether → 4,5-dichloro-2-methoxymethyl-2H-pyridazin-3-one
Reaction equation
[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)C(C)C)(C)C.[CH3:19][O:20][CH2:21]Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:9])[N:4]([CH2:19][O:20][CH3:21])[N:5]=[CH:6][C:7]=1[Cl:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
4,5-Dichloro-2H-pyridazin-3-one (30 g, 182 mmol), N,N-diisopropylethylamine (47.5 mL, 258 mmol) and 4-dimethylaminopyridine (2.20 g, 18.2 mmol) were dissolved in 200 mL of methylene chloride, to which was slowly added dropwise chloromethyl methyl ether (16.6 mL, 21.8 mmol) while maintaining at 0° C. The mixture was stirred for 3 h at room temperature. The reaction solution was washed with saturated aqueous sodium hydrogen carbonate solution, distilled under reduced pressure, and separated-purified by column chromatography (10% methylene chloride/ethyl acetate) to give the title compound (26.6 g, Yield: 70%) as a yellow solid.
Workup
- washThe reaction solution was washed with saturated aqueous sodium hydrogen carbonate solution
- distillationdistilled under reduced pressure
- customseparated-purified by column chromatography (10% methylene chloride/ethyl acetate)
Sources & evidence
- ORD record
- ord-1e8a5b17c8074463a49096be65b85ec9
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481537B2
Reaction notes
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