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

HRID 579240Notes

Reaction equation

HRID 579240 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:18])[C:13]([N:15]([CH3:17])[NH2:16])=[O:14])[CH3:2].[CH3:19][S:20]([CH2:22][C:23](=O)[CH3:24])=[O:21]>O1CCCC1>[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:18])[C:13]([N:15]([CH3:17])[N:16]=[C:23]([CH3:24])[CH2:22][S:20]([CH3:19])=[O:21])=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 125633731-Methylsulfinyl-2-propanoneHCID 569428781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine

Product 1

HCID 764690271-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfinyl-2-propylidene)hydrazineYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 50 ml volume three-necked flask, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39) (2.0 g), tetrahydrofuran (anhydrous) (5 ml), and 1-methylsulfinyl-2-propanone (7-1-1) (1.65 g) were added under a nitrogen atmosphere, and stirred at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure at room temperature. The residue was subjected to silica gel column chromatography (ethyl acetate to chloroform) to give 0.48 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. concentrationThe reaction mixture was concentrated under reduced pressure at room temperature

Sources & evidence

ORD record
ord-8a5b360d38e541e1a8d159a2beb1f2aa
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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