Imidazole → HCID 15753671, compound

HRID 894535Notes

Reaction equation

HRID 894535 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH:8]1(Br)[CH2:12][CH2:11][CH2:10][CH2:9]1.O>CN(C)C=O.CO>[CH:8]1([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 795Imidazole2×HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydride

Product 1

HCID 15753671HCID 15753671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

Imidazole (6.8 g, 0.1 mole) was dissolved in 100 ml of dry dimethylformamide (DMF). Sodium hydride, 50% dispersion in oil, (4.8 g, 0.1 mole) was added in small portions and the mixture was allowed to stir for 15 minutes. Cyclopentyl bromide (14.9 g, 0.1 mole) dissolved in 100 ml dry DMF was then added dropwise to the mixture which was kept under nitrogen and at about room temperature. Allowed to stir for a further 1 hour. When t.l.c. showed no further reaction, the mixture was poured onto approximately equal volume of water and shaken well. The product was then extracted with chloroform (3×200 ml) and dried over anhydrou MgSO4. The dry extract was evaporated down under vacuum. The DMF was then distilled off at 15 mmHg pressure to leave a yellowish oil. T.l.c. showed that the mixture was mainly product and an imidazole impurity, about 10 g nn on silica gel column with MeOH/EtOAC 1:9. Product fractions were combined and evaporated. Residual oil obtained was distilled under vacuum. B.pt. 67°-68° C./0.2 mm. Yield 2.0 g.

Workup

  1. additionwas then added dropwise to the mixture which
  2. customwas kept under nitrogen and at about room temperature
  3. stirringAllowed to stir for a further 1 hour
  4. customno further reaction
  5. stirringshaken well
  6. extractionThe product was then extracted with chloroform (3×200 ml)
  7. dry with materialdried over anhydrou MgSO4
  8. extractionThe dry extract
  9. customwas evaporated down under vacuum
  10. distillationThe DMF was then distilled off at 15 mmHg pressure
  11. customto leave a yellowish oil
  12. customevaporated
  13. customResidual oil obtained
  14. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-0cd6dc0d6f58442ab298a10b4618da60
Source dataset
uspto-grants-1981_08
Patent number
US04284641

Reaction notes

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