2,4,5-Triphenylimidazole → 1-(7-Bromoheptyl)-2,4,5-triphenylimidazole

HRID 265366

Reaction equation

HRID 265366 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:11]1[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:8]=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 102322,4,5-TriphenylimidazoleHCID 11430Potassium CarbonateHCID 783091,7-Dibromoheptane

Product 1

HCID 229163771-(7-Bromoheptyl)-2,4,5-triphenylimidazoleYield 61.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4,5-triphenylimidazole (11.5 g), 1,7-dibromo-heptane (50 g) and potassium carbonate (27 g) in dry butanone (250 ml) was heated at reflux for 20 hours. The mixture was filtered and the filtrate evaporated to an oil. Chromatography on silica gel (hexane/ethyl acetate) and recrystallisation from hexane gave 1-(7-bromoheptyl)-2,4,5-triphenylimidazole (11.3 g, 61.4%) as a colourless solid, m.p. 69°-71°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to an oil
  5. customChromatography on silica gel (hexane/ethyl acetate) and recrystallisation from hexane

Sources & evidence

ORD record
ord-20d0f6ec73f5498fbde81cc099d2687a
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Linked notes

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