3,4,6-Trichloropyridazine → 3,6-Dichloro-4-methanesulfonylpyridazine
Reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.[Na+].[CH3:11][S:12]([O-:14])=[O:13]>O.C1COCC1.CN(C=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[S:12]([CH3:11])(=[O:14])=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3,4,6-Trichloropyridazine (2.5 g; 13.6 mmol) and methanesulfinic acid sodium salt (2.78 g, 27.26 mmol) were stirred in 20 ml of a solvent mixture of water/THF/DMF (5:10:5) at RT for 30 h. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated ammonium chloride solution. The organic phase was removed and concentrated, and the crude product was purified by flash chromatography (dichloromethane:methanol). Yield: 1.4 g
Workup
- customThe solvent was removed under reduced pressure
- customthe residue was partitioned between ethyl acetate and saturated ammonium chloride solution
- customThe organic phase was removed
- concentrationconcentrated
- customthe crude product was purified by flash chromatography (dichloromethane:methanol)
Sources & evidence
- ORD record
- ord-f3c01bf9600a496c89aa13cb31eb9f0c
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08076336B2
Reaction notes
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