Imidazole → 1-pentylimidazole

HRID 894532Notes

Reaction equation

HRID 894532 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH3:5].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1>CO.[OH-].[Na+]>[CH2:1]([N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Conditions

Temperature
20 °C

Procedure

n-Pentylbromide (30 ml; 0.24 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 20° C. When the addition was complete the reaction mixture was stirred and refluxed for 24 hours. The solvent was evaporated, the residue extracted with chloroform (2×50 ml) and the solid remaining removed by filtration. The chloroform solution (filtrate) was dried over magnesium sulphate and concentrated to give a yellow oil which on purification gave 1-n-pentylimidazole as a colourless oil, b.p. 66°-68° C./0.15 mmHg.

Workup

  1. additionWhen the addition
  2. temperaturerefluxed for 24 hours
  3. customThe solvent was evaporated
  4. extractionthe residue extracted with chloroform (2×50 ml)
  5. customthe solid remaining removed by filtration
  6. dry with materialThe chloroform solution (filtrate) was dried over magnesium sulphate
  7. concentrationconcentrated
  8. customto give a yellow oil which
  9. customon purification

Sources & evidence

ORD record
ord-6341669658d448d090460a5fc7fbfcdf
Source dataset
uspto-grants-1981_08
Patent number
US04284641

Reaction notes

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