Tetrahydrofuran → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazine

HRID 335437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335437
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:14][NH:15][CH3:16])[CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][CH:3]=1.O1CCCC1.C(N(CC)CC)C.[CH2:29]([C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH2:38][CH3:39])[C:32]=1[C:40](=[O:44])[C:41](Cl)=[O:42])[CH3:30]>O>[CH2:29]([C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH2:38][CH3:39])[C:32]=1[C:40](=[O:44])[C:41]([N:15]([CH3:16])[N:14]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:42])[CH3:30]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 569427122-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl chlorideHCID 866893531-[1-(4-Fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazine

Produkt 1

HCID 866893541-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazineAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 30 ml volume two-necked flask, 1-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-2-methylhydrazine (5-2-4) (0.90 g) and anhydrous tetrahydrofuran (5 ml) were added under a nitrogen atmosphere, and added triethylamine (0.37 g) under cooling. To the mixture, 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl chloride (6-a) (0.88 g) was added dropwise below 0° C., and stirred under ice-cooling for 2 hours. The reaction mixture was added to water, and extracted with tert-butyl methyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (tert-butyl methyl ether) to give 1.0 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-[1-(4-fluorophenyl)-2-methylsulfonylethylidene]-1-methylhydrazine ((4-64)-(1)-39).

Aufarbeitung

  1. temperatureunder cooling
  2. temperaturecooling for 2 hours
  3. extractionextracted with tert-butyl methyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (tert-butyl methyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-e665272c55cc46deb18993aed587ce96
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884010B2

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