Hydrochloric Acid → 5-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione

HRID 1857509

Reaktionsgleichung

Reaktionsgleichung von HRID 1857509
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:26]=[CH:25][C:20](/[CH:21]=[CH:22]/[CH:23]=O)=[CH:19][CH:18]=1.[O:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33].N1CCCCC1.Cl>O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=2)=[N:4][C:3]=1[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[CH:22][CH:23]=[C:31]2[O:27][C:28](=[O:33])[NH:29][C:30]2=[O:32])=[CH:25][CH:26]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 15485649(E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamaldehyde

Produkt 1

HCID 570370095-[4-[2-[5-Methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedioneAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamaldehyde (1.20 g), 2,4-oxazolidinedione (0.525 g), piperidine (0.09 g) and ethanol (20 ml) was heated for 5 hours under reflux. The reaction mixture was poured into water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and, then, concentrated. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-methanol (50:1) was obtained 5-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamylidene]-2,4-oxazolidinedione (0.51g, 34%). Recrystallization from dichloromethane-methanol gave pale yellow prisms, m.p.213-214° C.

Aufarbeitung

  1. temperaturewas heated for 5 hours
  2. temperatureunder reflux
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe concentrate was purified by means of a silica gel column chromatography
  8. washFrom the fractions eluted with chloroform-methanol (50:1)

Quellen und Nachweise

ORD-Eintrag
ord-099744c7160b44198edfebd72e90bc50
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147099

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