2,4,5-Triphenylimidazole → HCID 86751077, compound

HRID 265355

Reaction equation

HRID 265355 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 86751077HCID 86751077, compoundYield 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 filtrate 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 filtrate 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 filtrate was evaporated to dryness in vacuo
  7. filtrationunreacted 2,4,5-triphenylimidazole was collected by filtration (3.1 g)
  8. temperatureThe filtrate was cooled
  9. customa white precipitate was collected
  10. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-de315edf787b4354befe83bbfa06f099
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Linked notes

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