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

HRID 579270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579270
[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-2ecd3aa1b7084574807842d61f28502c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040709B2

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