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

HRID 1376341Notes

Reaction equation

HRID 1376341 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 flitrate 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 flitrate evaporated to an oil
  5. customChromatography on silica gel (hexane/ethyl acetate) and recrystallisation from hexane

Sources & evidence

ORD record
ord-e3b3e84f4fe040bbb13ac8d5591c4411
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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