2,4,5-Triphenylimidazole → 1-(7-Ethoxy-carbonyl-heptyl)-2,4,5-triphenylimidazole

HRID 1376331Notes

Reaction equation

HRID 1376331 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.BrC[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=O.[C:37](=O)([O-])[O-:38].[K+].[K+]>CC(=O)CC>[CH2:35]([O:34][C:32](=[C:37]=[O:38])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][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)[CH3:36]

Participants

5

Reactant 3

HCID 102322,4,5-TriphenylimidazoleHCID 11430Potassium CarbonateHCID 264813Ethyl 8-bromooctanoate

Product 1

HCID 867510771-(7-Ethoxy-carbonyl-heptyl)-2,4,5-triphenylimidazoleYield 48.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4,5-triphenylimidazole (11 g), ethyl 8-bromooctanoate (18.64 g), anhydrous potassium carbonate (51.3 g) and dry butanone (350 ml ) was heated at reflux for 26 h. The cooled reaction mixture was filtered to remove inorganics and the flitrate was evaporated to dryness in vacuo. The residue was stirred in hexane and unreacted 2,4,5-triphenylimidazole was collected by filtration (3.1 g). The flitrate was cooled and a white precipitate was collected. Recrystallisation from hexane gave 1-(7-ethoxy-carbonyl-heptyl)-2,4,5-triphenylimidazole (8.37 g, 48.4%) as a white solid, m.p. 65°-7°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 26 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customto remove inorganics
  6. customthe flitrate was evaporated to dryness in vacuo
  7. filtrationunreacted 2,4,5-triphenylimidazole was collected by filtration (3.1 g)
  8. temperatureThe flitrate was cooled
  9. customa white precipitate was collected
  10. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-9300d15c1bc64fae824eae0d6cce320f
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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