Formaldehyde → HCID 68834641, Verbindung

HRID 47240

Reaktionsgleichung

Reaktionsgleichung von HRID 47240
[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.C=O.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].[CH3:24]CCCCC>CCO>[CH2:19]([NH:23][CH2:24][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7](=[CH:6][C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[C:8]1=[O:16])[CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 8007ButylamineHCID 8058HexaneHCID 5908088(Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-one

Produkt 1

HCID 68834641HCID 68834641, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (120.0 mg, 0.571 mmol), paraformaldehyde (17.1 mg, 0.571 mmol), and butylamine (56.4 μL, 0.571 mmol) in 5.5 mL of EtOH was heated at reflux for 2.5 h. Then reaction mixture was treated with 2 mL of hexane was and then cooled to 0° C. The reaction mixture was then filtered to remove Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one. The filtrate was partitioned between dilute HCl and ethyl acetate. The organic layer was removed and the aqueous layer washed with 15 mL Ethyl acetate. The aqueous phase was made basic to pH 8 with saturated NaHCO3 and extracted with ethyl acetate. The ethyl acetate layer was washed with H2O, brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo to give 58 mg of yellow oil. The oil was purified by chromatography (silica gel, 1:1/hexane:ethyl acetate) to give the title compound (51.6 mg, 31%) as a yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. customThen reaction mixture
  4. filtrationThe reaction mixture was then filtered
  5. customto remove Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one
  6. customThe filtrate was partitioned between dilute HCl and ethyl acetate
  7. customThe organic layer was removed
  8. washthe aqueous layer washed with 15 mL Ethyl acetate
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with H2O, brine
  11. dry with materialdried over anhydrous Na2SO4
  12. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-df79f2cf7a9b4263834f59cd3ebdf5e4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699863B1

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