Methyl Ethyl Ketone → 1,4,5-Triphenyl-3-(7-bromoheptyl)imidazol-2-one

HRID 265351

Reaktionsgleichung

Reaktionsgleichung von HRID 265351
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:9][C:8]2=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:25][C:26](Br)(CCC)[CH2:27][CH2:28]C.C(=O)([O-])[O-].[K+].[K+].[CH3:40][C:41](=O)[CH2:42][CH3:43]>>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:28][CH2:27][CH2:26][Br:25])[C:8]2=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 6285441,4,5-Triphenyl-1,3-dihydro-2H-imidazol-2-oneHCID 216791024,4-Dibromoheptane

Produkt 1

HCID 229163881,4,5-Triphenyl-3-(7-bromoheptyl)imidazol-2-oneAusbeute 46 %

Versuchsvorschrift

A mixture of 1,4,5-triphenylimidazol-2-one (15.3 g), dibromoheptane (50.6 g) and potassium carbonate (13.8 g) was heated at reflux temperature in dry butanone (750 ml) for 20 hours. The mixture was cooled, filtered and the filtrate evaporated to an oil which was chromatographed on silica gel (hexane/ethyl acetate) to give 1,4,5-triphenyl-3-(7-bromoheptyl)imidazole-2-one (11.1 g, 46%) as an oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to an oil which
  5. customwas chromatographed on silica gel (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-37c6d3059e04483fafa6f3e031bbe891
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648373

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