Imidazole → HCID 20550244, compound

HRID 894527Notes

Reaction equation

HRID 894527 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8]Br)[CH2:4][CH2:3]1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.CC(C)([O-])C.[K+]>C(O)CCC>[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 134603641-(Bromomethyl)-4-methylcyclohexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 20550244HCID 20550244, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Methylcyclohexylmethyl bromide (3.1 g; 0.0164 M) was added dropwise to a refluxing solution of imidazole (1.12 g; 0.0165 M) in a solution of potassium tertiary butoxide (1.85 g; 0.0165 M) in n-butanol (50 cm3). The reaction mixture was kept under dry nitrogen. After addition the mixture was heated under reflux for a further 2 hours and stood overnight at room temperature. TLC showed reaction half complete. The mixture was refluxed for a further 8 hours and stood over weekend at room temperature. TLC showed no further reaction was occurring. Insoluble material was filtered off, and solvent removed under vacuum. Residue taken up in 2 N-HCl (100 cm3) and washed with ether (50 ml). Aqueous layer basified with excess 10 N NaOH and extracted with chloroform (3×50 cm3). Combined extracts were dried over anhydrous MgSO4 and solvent removed under vacuum. Oily residue was run on a silica gel column and eluted with EtOAc/MeOH 9:1. 0.8 g of column product obtained and was distilled to give 0.28 g of pure product having b.p. 80° C. at 0.125 mmHg.

Workup

  1. additionAfter addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for a further 2 hours
  4. customreaction half complete
  5. temperatureThe mixture was refluxed for a further 8 hours
  6. waitstood over weekend at room temperature
  7. customno further reaction
  8. filtrationInsoluble material was filtered off
  9. customsolvent removed under vacuum
  10. washwashed with ether (50 ml)
  11. extractionextracted with chloroform (3×50 cm3)
  12. dry with materialCombined extracts were dried over anhydrous MgSO4 and solvent
  13. customremoved under vacuum
  14. washeluted with EtOAc/MeOH 9:1
  15. custom0.8 g of column product obtained
  16. distillationwas distilled

Sources & evidence

ORD record
ord-75fc7754ae994b6cb654d37b80d37d42
Source dataset
uspto-grants-1981_08
Patent number
US04284641

Reaction notes

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