Formaldehyde → HCID 68865887, Verbindung

HRID 47237

Reaktionsgleichung

Reaktionsgleichung von HRID 47237
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[C:8](=[O:16])[NH:9][C:10]2[C:15]\1=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=O.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O1CCOCC1.CCO>[N:19]1([CH2:17][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[CH:6][C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)[C:8]2=[O:16])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Komponenten

6

Edukt 3

HCID 712Formaldehyde2×HCID 8083Morpholine2×HCID 5908088(Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-one

Produkt 1

HCID 68865887HCID 68865887, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (120 mg, 0.57 mmol), paraformaldehyde (32 mg, 1.1 mmol), and morpholine (62.2 μL, 0.71 mmol) in 8.0 mL of 20% dioxane in EtOH was heated at reflux for 19.5 h. The reaction mixture was concentrated and paraformaldehyde (10.0 mg, 0.33 mmol), morpholine (15 μL, 0.17 mmol) and EtOH (7 mL) was added. The reaction mixture refluxed for 24 h. The reaction mixture was cooled to room temperature and concentrated. The residue was dissolved in 15 mL of CHCl3 and treated with activated charcoal. The resulting suspension was filtered and the filtrate concentrated. The residue was crystallization from ethyl acetate/hexane to give the title compound (88.0 mg, 50%) as a bright yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 19.5 h
  3. concentrationThe reaction mixture was concentrated
  4. temperatureThe reaction mixture refluxed for 24 h
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 15 mL of CHCl3
  7. additiontreated with activated charcoal
  8. filtrationThe resulting suspension was filtered
  9. concentrationthe filtrate concentrated
  10. customcrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-7796d9be31304c5281081c9b2e12dd9e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699863B1

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