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Acetic Acid → HCID 9912511, Verbindung

HRID 2299878
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2299878
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.O=[C:25]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:26][CH2:27][C:28]([NH2:30])=[O:29].C(O)(=O)C.C([O-])(=O)C.[Na+]>O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:25](\[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)/[CH2:26][CH2:27][C:28]([NH2:30])=[O:29])=[CH:22][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 5200224-Oxo-4-phenylbutanamideHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Produkt 1

HCID 9912511HCID 9912511, VerbindungAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (1.00 g), 4-oxo-4-phenylbutanamide (571 mg), acetic acid (0.553 ml), sodium acetate (528 mg) and ethanol (20 ml) was heated to reflux for 10 hours, the mixture was cooled to room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography and concentrated a portion from an ethyl acetate-hexane (3:1, v/v)-eluted fraction which eluted following the E-compound, to obtain crystals. The crystals were recrystallized from ethanol to obtain Z-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutanamide (120 mg, yield 8%) as colorless crystals. m.p. 110-112° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 10 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. concentrationconcentrated a portion from an ethyl acetate-hexane (3:1, v/v)-eluted fraction which
  8. washeluted
  9. customto obtain crystals
  10. customThe crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8edaba6b8a1c43b491ea757110b86549
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06495581B1

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