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Acetic Acid → HCID 70091973, Verbindung

HRID 1197130
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1197130
[CH3:1][C:2]1[N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=[N:4][C:3]=1[CH:26]=[C:27]1[C:40](=[O:41])[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][C:30]=2[CH2:29][CH2:28]1.[C:42]([OH:45])(=[O:44])[CH3:43].[OH2:46].Cl>C1COCC1>[C:40]([OH:41])(=[O:46])/[CH:27]=[CH:43]\[C:42]([OH:45])=[O:44].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:26][CH:27]1[C:40](=[O:41])[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][C:30]=2[CH2:29][CH2:28]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 53721853HCID 53721853, Verbindung

Produkt 1

HCID 70091973HCID 70091973, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1,2-dihydro-3-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methylene]-4(3H)-phenanthrenone (0.5 g) in a mixture of THF (15 ml), acetic acid (5 ml) and water (5 ml) was heated on a steam bath for 45 min. 0.5M Hydrochloric acid (25 ml) was added and the mixture was extracted with ether (2×15 ml; discarded). The aqueous solution was basified with solid potassium carbonate and the mixture was extracted with dichloromethane (3×15 ml). The dried extracts were evaporated and the residue (0.21 g) was dissolved in ethanol (25 ml) and hydrogenated at room temperature and atmospheric pressure over a stirred suspension of 10% palladium on carbon (0.05 g) for 1.5 h. The solution was filtered and the filtrate evaporated to give a gum which was purified by FCC eluting firstly with ethyl acetate and then with ethyl acetate/methanol (3:1) to give the free base of the title compound as a gum (0.13 g). This was dissolved in methanol (20 ml) containing maleic acid (50 mg) and the solution was evaporated to give a gum which on trituration with ether gave the title compound as a solid (0.11 g), m.p. 133°-134° .

Aufarbeitung

  1. temperaturewas heated on a steam bath for 45 min
  2. extractionthe mixture was extracted with ether (2×15 ml; discarded)
  3. extractionthe mixture was extracted with dichloromethane (3×15 ml)
  4. customThe dried extracts were evaporated
  5. dissolutionthe residue (0.21 g) was dissolved in ethanol (25 ml) and hydrogenated at room temperature
  6. additionatmospheric pressure over a stirred suspension of 10% palladium on carbon (0.05 g) for 1.5 h
  7. filtrationThe solution was filtered
  8. customthe filtrate evaporated
  9. customto give a gum which
  10. customwas purified by FCC
  11. washeluting firstly with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0e39a3d03a724e259e25455f2108fa9b
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05116984

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