Tetrahydrofuran → 1-[2-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine

HRID 335456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335456
[CH3:1][NH:2][N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7].O1CCCC1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][C:33]([CH2:41][CH3:42])=[C:34]([C:36](=[O:40])[C:37](Cl)=[O:38])[CH:35]=2)=[CH:26][CH:25]=1>CCCCCC>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][C:33]([CH2:41][CH3:42])=[C:34]([C:36](=[O:40])[C:37]([N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])=[O:38])[CH:35]=2)=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 569425572-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetyl chlorideHCID 764689591-Methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine

Produkt 1

HCID 866893601-[2-[5-(4-Chlorophenyl)-2-ethylphenyl]-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazineAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a 25 ml volume three-necked flask, 1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine (5-2-1) (670 mg), tetrahydrofuran (anhydrous) (2.25 ml), and triethylamine (390 mg) were added under a nitrogen atmosphere. To the mixture, 2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetyl chloride (6-c) (937 mg) was added dropwise at 0° C. and stirred for 2 hours. To hexane (15 ml) in a 50 ml volume three-necked flask, the reaction mixture was added dropwise, stirred for 10 minutes, and filtered. The residue was dried under reduced pressure, dissolved in ethyl acetate, and filtered again. The filtrate was concentrated under reduced pressure to give 853 mg of 1-[2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-67). The filtrate from the first filtration was concentrated under reduced pressure, the residue was subjected to column chromatography (hexane:ethyl acetate=1.5:1) to give 240 mg of additional 1-[2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-67).

Aufarbeitung

  1. stirringstirred for 10 minutes
  2. filtrationfiltered
  3. customThe residue was dried under reduced pressure
  4. dissolutiondissolved in ethyl acetate
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bed44b6d67be4308b75485701264be63
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884010B2

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