2,4,5-Triphenylimidazole → 9-(1,2,4-Tri-phenylimidazolyl)-2,2-dimethylnonanoic acid

HRID 265391

Reaction equation

HRID 265391 reaction equation
[C:1]1([C:7]2[NH:8][C:9](C3C=CC=CC=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[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([CH3:39])([CH3:38])[C:33]([O:35]CC)=[O:34].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>CS(C)=O.CC(=O)CC>[C:1]1([N:8]2[C:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([CH3:38])([CH3:39])[C:33]([OH:35])=[O:34])=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 102322,4,5-TriphenylimidazoleHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 11369854Nonanoic acid, 9-bromo-2,2-dimethyl-, ethyl ester

Product 1

HCID 541257209-(1,2,4-Tri-phenylimidazolyl)-2,2-dimethylnonanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4,5-triphenylimidazole (4.13 g), ethyl 9-bromo-2,2-dimethylnonanoate (10.95 g), potassium carbonate (10 g) and 2-butanone was stirred at reflux for 48 hours. The mixture was filtered, solvent removed under reduced pressure and the residue was chromatographed on silica gel eluted with chloroform to give a clear oil which was dissolved in dimethyl sulphoxide (30 ml) and treated with potassium hydroxide (3 g). The mixture was stirred at 40° C. for 24 hours when the solvent was removed under reduced pressure. Water (50 ml) was added, the pH of the solution was adjusted to 4 and the aqueous was extracted with chloroform (3×50 ml). The chloroform extracts were dried over magnesium sulphate, filtered and the solvent removed to give a solid which was recrystallised from acetonitrile to give 9-(1,2,4-tri-phenylimidazolyl)-2,2-dimethylnonanoic acid as a white crystalline solid, m.p. 119°-120° C.; Found: C, 79.85; H, 7.64; N, 6.23% (C32H36N2O2); Requires: C, 79.96; H, 5.54; N, 5.82%

Workup

  1. temperatureat reflux for 48 hours
  2. filtrationThe mixture was filtered
  3. customsolvent removed under reduced pressure
  4. customthe residue was chromatographed on silica gel
  5. washeluted with chloroform
  6. customto give a clear oil which
  7. stirringThe mixture was stirred at 40° C. for 24 hours when the solvent
  8. customwas removed under reduced pressure
  9. additionWater (50 ml) was added
  10. extractionthe aqueous was extracted with chloroform (3×50 ml)
  11. dry with materialThe chloroform extracts were dried over magnesium sulphate
  12. filtrationfiltered
  13. customthe solvent removed
  14. customto give a solid which
  15. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-2dea89c048ee41a98d6ced51432650ff
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Linked notes

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