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Benzaldehyde → 4H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-

HRID 845100
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 845100
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([C:21]1[O:26][C:25](=[O:27])[C:24]2[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=2[N:22]=1)[C:10]1[O:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]=1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH:5]1[CH:6]=[CH:7][C:2]([CH:1]=[C:9]([C:10]2[O:15][C:14](=[O:16])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=2)[C:21]2[O:26][C:25](=[O:27])[C:24]3[C:23](=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:22]=2)=[CH:3][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 13650289HCID 13650289, Verbindung

Produkt 1

HCID 30638134H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

Benzaldehyde (259 mg, 2.45 mmol), Compound (2,2'-methylenebis(3,1-benzoxazine-4-one) (500 mg, 1.63 mmol), and BF3. (C2H5)2O (0.045 ml, 0.163 mmol) were heated under reflux in dry toluene (20 ml) for 20 hours. After the reaction, the solvent was removed under reduced pressure from the reaction mixture, the residue was treated with water, extracted with benzene, and the organic layer was separated, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in the developing solvent and adsorbed on silica gel, and was purified by column chromatography to give the desired compound 52. The obtained product was crystallized from isopropylether to give the desired compound 52 in white solid in a good yield. m.p., IR, and NMR spectra of the product fully agreed with those of the one obtained in Example 19.

Aufarbeitung

  1. customAfter the reaction
  2. customthe solvent was removed under reduced pressure from the reaction mixture
  3. additionthe residue was treated with water
  4. extractionextracted with benzene
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionThe residue was dissolved in the developing solvent
  10. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fbb00ec6feb4434ab0bceb8b4e3e0e82
Quelldatensatz
uspto-grants-1988_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04755506

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