Water → 4-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone
Reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:6]=1[C:14](=O)[C:15]([N:17]([CH3:24])[N:18]=[C:19]([CH3:23])[CH2:20][S:21][CH3:22])=[O:16])[CH3:4].O>O1CCCC1>[CH2:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:6]=1[C:14]1[C:15](=[O:16])[N:17]([CH3:24])[N:18]=[C:19]([CH3:23])[C:20]=1[S:21][CH3:22])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 200 ml volume four-necked flask, tetrahydrofuran (anhydrous) (27.0 ml) and sodium hydride (1.90 g) were added under a nitrogen atmosphere at about 0° C., and stirred. Then, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine ((4-4)-(1)-39) (14.2 g) dissolved in tetrahydrofuran (anhydrous) (45 ml) was added dropwise over 30 minutes, and then the mixture was stirred at 0° C. for 2 hours. Then, to the mixture was added water (100 ml) at room temperature, and extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=4:1) to give 5.45 g of 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone.
Workup
- additionwas added dropwise over 30 minutes
- stirringthe mixture was stirred at 0° C. for 2 hours
- extractionextracted with tert-butyl methyl ether
- concentrationThe organic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8827ffb1b88948b5b35fcaf23ba62f62
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040709B2
Reaction notes
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