Imidazole → HCID 454103, compound

HRID 1690710Notes

Reaction equation

HRID 1690710 reaction equation
N1C=CN=C1.C[O:7][C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[NH:21][CH:22]=[CH:23][N:24]=1>>[NH:21]1[CH:22]=[CH:23][N:24]=[C:20]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([OH:25])=[O:7]

Participants

3

Reactant 2

HCID 795ImidazoleHCID 66905235HCID 66905235, compound

Product 1

HCID 454103HCID 454103, compound

Procedure

To this end, 12-bromo-1-dodecanol is oxidized with Jones' reagent to form 12-bromo-1-dodecanoic acid. Then the white solid acid is esterified with diazomethane to form the corresponding methyl ester. The methyl ester is treated directly with imidazole and reacted at 80° C. for five hours until it forms 12-imidazolyl-1-dodecanoic acid methyl ester. The thick mass, which is obtained in this way, is split between water and dichloromethane; and the organic phase is dried over Na2SO4 and concentrated by evaporation. The oily residue is cleaned chromatographically on silica gel and then dissolved in a mixture of methanol and tetrahydrofuran (3:4), treated with LiOH.H2O, and the mixture is heated under reflux for two hours. Following evaporation of the solvent, the white residue is dissolved again in water, extracted with dichloromethane, acidified to a pH 5-6, and extracted again with ethyl acetate. The ethyl acetate extract is dried over Na2SO4, filtered and concentrated by evaporation. The white solid is recrystallized from methanol/ether and yields 12-imidazolyl-1-dodecanoic acid.

Workup

  1. customreacted at 80° C. for five hours until it
  2. customThe thick mass, which is obtained in this way
  3. customis split between water and dichloromethane
  4. dry with materialand the organic phase is dried over Na2SO4
  5. concentrationconcentrated by evaporation
  6. dissolutiondissolved in a mixture of methanol and tetrahydrofuran (3:4)
  7. additiontreated with LiOH.H2O
  8. temperaturethe mixture is heated
  9. temperatureunder reflux for two hours
  10. customevaporation of the solvent
  11. dissolutionthe white residue is dissolved again in water
  12. extractionextracted with dichloromethane
  13. extractionextracted again with ethyl acetate
  14. extractionThe ethyl acetate extract
  15. dry with materialis dried over Na2SO4
  16. filtrationfiltered
  17. concentrationconcentrated by evaporation
  18. customThe white solid is recrystallized from methanol/ether

Sources & evidence

ORD record
ord-74d7da6ecdf14a03a515e6936712b710
Source dataset
uspto-grants-2012_04
Patent number
US08153676B2

Reaction notes

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