Imidazole → 1-Cyclohexylmethylimidazole

HRID 894533Notes

Reaction equation

HRID 894533 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.[Na]>C(O)C>[CH:3]1([CH2:2][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 137636Cyclohexane, (bromomethyl)-HCID 5360545Sodium

Product 1

HCID 201484651-Cyclohexylmethylimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromomethylcyclohexane (39.8 g; 0.225 mole) was added dropwise to a refluxing solution of imidazole (13.6 g; 0.2 mole) and sodium (4.6 g; 0.2 mole) in absolute ethanol (100 ml). After addition the reaction mixture was heated under reflux for a further 5 hours. After this period the mixture was cooled and the solvent evaporated under reduced pressure. The residue was taken up in water (150 ml), washed with ether (50 ml) and extracted with chloroform (3×50 ml). The combined chloroform extracts were dried over anhydrous magnesium sulphate and evaporated under reduced pressure to leave a residual yellow oil as crude product which was purified to give the product as a colourless oil b.p. 86°-90° C./0.2 mmHg. The product solidified on cooling, m.p. 25° to 30° C.

Workup

  1. additionAfter addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for a further 5 hours
  4. temperatureAfter this period the mixture was cooled
  5. customthe solvent evaporated under reduced pressure
  6. washwashed with ether (50 ml)
  7. extractionextracted with chloroform (3×50 ml)
  8. dry with materialThe combined chloroform extracts were dried over anhydrous magnesium sulphate
  9. customevaporated under reduced pressure
  10. customto leave a residual yellow oil as crude product which
  11. customwas purified

Sources & evidence

ORD record
ord-d87de7715793409692337e43e3a58572
Source dataset
uspto-grants-1981_08
Patent number
US04284641

Reaction notes

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