Acetophenone → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-phenyl-1-ethylidene)hydrazine

HRID 335465

Reaktionsgleichung

Reaktionsgleichung von HRID 335465
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:17])[C:13]([NH:15][NH2:16])=[O:14])[CH3:2].C1COCC1.[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)[CH3:24]>C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:17])[C:13]([NH:15][N:16]=[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:24])=[O:14])[CH3:2]

Komponenten

5

Edukt 3

HCID 7410AcetophenoneHCID 8028TetrahydrofuranHCID 569428732-(2,6-Diethyl-4-methylphenyl)-2-oxoacetohydrazide

Produkt 1

HCID 866893611-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-phenyl-1-ethylidene)hydrazineAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a 50 mL volume two-necked flask, 3.0 g of 2-(2,6-diethyl-4-methylphenyl)-2-oxoacetohydrazide ((12-1)-(11)-39), 20 ml of THF (anhydrous), 1.73 g of acetophenone and 780 mg of acetic acid were added under a nitrogen atmosphere, and the mixture was stirred for 6 hours under reflux. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Water was added to the residue and the resultant was extracted with t-butyl methyl ether. The organic layer was concentrated under reduced pressure and hexane was added thereto. The precipitated crystals were collected by filtration and dried to give 3.77 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(1-phenyl-1-ethylidene)hydrazine ((40-a)-(14)-7).

Aufarbeitung

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe resultant was extracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated under reduced pressure and hexane
  6. additionwas added
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1e9b6b45e51847d59ef193e706f32213
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884010B2

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