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Water → 4-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone

HRID 335416
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 335416
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 24758Sodium hydrideHCID 764689581-(2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl)-1-methyl-2-(1-methylsulfanyl-2-propylidene)hydrazine

Produkt 1

HCID 569428794-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinoneAusbeute 40,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added dropwise over 30 minutes
  2. stirringthe mixture was stirred at 0° C. for 2 hours
  3. extractionextracted with tert-butyl methyl ether
  4. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a1b02b4743534a4d8497a2eb4d3b9091
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08884010B2

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