Sodium Sulfite → 4-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

HRID 335417Notes

Reaction equation

HRID 335417 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:22])[N:14]([CH3:21])[N:15]=[C:16]([CH3:20])[C:17]=1SC)[CH3:2].[C:23](=O)([O-])O.[Na+].ClC1C=CC=C(C(OO)=O)C=1.[S:39]([O-:42])([O-])=[O:40].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:22])[N:14]([CH3:21])[N:15]=[C:16]([CH3:20])[C:17]=1[S:39]([CH3:23])(=[O:42])=[O:40])[CH3:2]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 569428794-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone

Product 1

HCID 569427174-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 20 ml volume two-necked flask, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone ((2-4)-(1)-39) (0.18 g), chloroform (1.0 ml), and sodium hydrogen carbonate (0.20 g) were added thereto under a nitrogen atmosphere. Meta-chloroperbenzoic acid (0.32 g) was added thereto at room temperature, and then the mixture was stirred for 4 hours. After stirring, to the reaction mixture was added saturated aqueous sodium sulfite solution, and extracted with tert-butyl methyl ether. Then, the organic layer was concentrated under reduced pressure. Then, the residue was subjected to column chromatography (silica gel 10 g, chloroform:ethyl acetate=15:1) to give 0.12 g of 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-39).

Workup

  1. stirringAfter stirring, to the reaction mixture
  2. extractionextracted with tert-butyl methyl ether
  3. concentrationThen, the organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d46da4bec364b21a5bb962be08b74c8
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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