3,4,6-Trichloropyridazine → 3,6-Dichloro-4-methanesulfonylpyridazine

HRID 657927Notes

Reaction equation

HRID 657927 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

HCID 951233,4,6-TrichloropyridazineHCID 2733271Sodium methanesulfinate

Product 1

HCID 580457893,6-Dichloro-4-methanesulfonylpyridazine

Reagents, catalysts & solvents 1

HCID 86606902water THF DMFSolvent

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

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated ammonium chloride solution
  3. customThe organic phase was removed
  4. concentrationconcentrated
  5. 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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