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

HRID 1742274Notes

Reaction equation

HRID 1742274 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-8714938ddf3e40baa6de6386f1d32b9d
Source dataset
uspto-grants-1994_08
Patent number
US05338752

Reaction notes

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