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

HRID 1524520Notes

Reaction equation

HRID 1524520 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-2a4c6fcd11624d588d842a8da755c32f
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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