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

HRID 265351

Reaction equation

HRID 265351 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-37c6d3059e04483fafa6f3e031bbe891
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Linked notes

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