Imidazole → Butylimidazole

HRID 894528Notes

Reaction equation

HRID 894528 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[NH:6]1[CH:10]=[CH:9][N:8]=[CH:7]1>CO.[OH-].[Na+]>[CH2:2]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 795ImidazoleHCID 8002Butyl bromide

Product 1

HCID 61347Butylimidazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Bromobutane (27.4 ml; 0.255 mole) was added dropwise to a stirred solution of imidazole (13.6 g; 0.2 mole) in a mixture of methanol (30 ml) and sodium hydroxide solution (30 ml; 10M) maintained at 30° to 40° C. When the addition was complete the reaction mixture was stirred and refluxed for 12 hours. The solvent was evaporated, the residue extracted with chloroform (2×50 ml) and the extracts dried over magnesium sulphate and concentrated under reduced pressure. The resulting yellow oil was purified to give 1-n-butylimidazole as a colourless oil, b.p. 122°-123° C./20 mmHg.

Workup

  1. temperaturemaintained at 30° to 40° C
  2. additionWhen the addition
  3. temperaturerefluxed for 12 hours
  4. customThe solvent was evaporated
  5. extractionthe residue extracted with chloroform (2×50 ml)
  6. dry with materialthe extracts dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting yellow oil was purified

Sources & evidence

ORD record
ord-365b62116e4e4a3690247b253e308d6e
Source dataset
uspto-grants-1981_08
Patent number
US04284641

Reaction notes

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