Potassium Carbonate → 1,4,5-Triphenyl-2-(6-bromohexyloxy)imidazole

HRID 1376370Notes

Reaction equation

HRID 1376370 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][CH:26](Br)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[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][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][Br:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6285441,4,5-Triphenyl-1,3-dihydro-2H-imidazol-2-oneHCID 118068541,1-Dibromohexane

Product 1

HCID 229163701,4,5-Triphenyl-2-(6-bromohexyloxy)imidazoleYield 29.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1,4,5-triphenylimidazol-2-one (6.25 g), dibromohexane (24.4 g) and potassium carbonate (5.53 g) in dry butanone (300 ml) was heated at reflux temperature for 24 hours. The mixture was cooled and the flitrate evaporated to an oil which was chromatographed on silica gel (hexaneyethyl acetate) to give 1,4,5-triphenyl-2-(6-bromohexyloxy)-imidazole (2.8 g, 29%) as a white solid, m.p. 87°-9° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hours
  3. temperatureThe mixture was cooled
  4. customthe flitrate evaporated to an oil which
  5. customwas chromatographed on silica gel (hexaneyethyl acetate)

Sources & evidence

ORD record
ord-c1815394dbf94b439126ecf3461fd303
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

Loading…