Diisopropylethylamine → HCID 68573992, Verbindung

HRID 225496

Reaktionsgleichung

Reaktionsgleichung von HRID 225496
[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]([NH2:18])=[NH:17])[CH:2]=[CH2:3].CN(C)[CH:21]=[CH:22][C:23]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=O.C(N(C(C)C)C(C)C)C>C(O)CCC.C(OCC)(=O)C>[CH2:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]1[N:18]=[C:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[CH:21][N:17]=1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178459007HCID 178459007, Verbindung

Produkt 1

HCID 68573992HCID 68573992, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A stirred mixture of {2-[(2-propenyloxy)-methyl]-5-nitro-phenyl}-guanidine (3.75 g, 15 mmol), 3-(dimethylamino)-1-(3-pyridinyl)-2-propen-1-one (2.60 g, 15 mmol) and ethyl diisopropylamine (2.6 mL, 15 mmol) in 1-butanol (50 mL) is heated at 120° C. for 20 h. The solvent is then evaporated off under reduced pressure to give a residue which is dissolved in ethyl acetate (100 mL). The resulting mixture is filtered (celite), washed with saturated aqueous sodium chloride (50 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate, and recrystallised from ethyl acetate-hexane to give the title compound as a yellow crystalline solid, m.p. 213-2150C.

Aufarbeitung

  1. customThe solvent is then evaporated off under reduced pressure
  2. customto give a residue which
  3. filtrationThe resulting mixture is filtered (celite)
  4. washwashed with saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product which
  9. customis purified by column chromatography on silica gel, eluent ethyl acetate
  10. customrecrystallised from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-56d4ff03fd554ab5ade9deb49f7d226d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557105B2

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