Methyl Ethyl Ketone → 1,4,5-Triphenyl-2-(7-bromoheptyloxy)imidazole

HRID 265399

Reaktionsgleichung

Reaktionsgleichung von HRID 265399
[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]=[C:8]2[O:24][CH2:40][CH2:41][CH2:42][CH2:43][CH2:28][CH2:27][CH2:26][Br:25])[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 229164121,4,5-Triphenyl-2-(7-bromoheptyloxy)imidazoleAusbeute 21 %

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-2-(7-bromoheptyloxy)imidazole (5.0 g, 21%) as a white solid, m.p. 97°-9° C.

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-0cef1b1cd8b2483ca68397192a695509
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648373

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