Hydrogen Peroxide → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfinyl-2-propylidene)hydrazine

HRID 335427Notes

Reaction equation

HRID 335427 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](=[O:23])[C:13]([N:15]([CH3:22])[N:16]=[C:17]([CH3:21])[CH2:18][S:19][CH3:20])=[O:14])[CH3:2].[OH:24]O>CO>[CH2:10]([C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:12](=[O:23])[C:13]([N:15]([CH3:22])[N:16]=[C:17]([CH3:21])[CH2:18][S:19]([CH3:20])=[O:24])=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 764689581-(2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl)-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine

Product 1

HCID 764690271-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfinyl-2-propylidene)hydrazineYield 33.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 50 ml volume three-necked flask, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine ((4-4)-(1)-39) (5.60 g) and methanol (14 ml) were added, and cooled on ice-bath. 33% of aqueous hydrogen peroxide solution (2.1 g) was added dropwise thereto. Then, the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate to chloroform) to give 1.95 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfinyl-2-propylidene)hydrazine ((4-19)-(1)-39).

Workup

  1. temperaturecooled on ice-bath
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c733235acfa84ae3a6465309f9a2ac32
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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