Imidazole → 1-pentylimidazole
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
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- additionWhen the addition
- temperaturerefluxed for 24 hours
- customThe solvent was evaporated
- extractionthe residue extracted with chloroform (2×50 ml)
- customthe solid remaining removed by filtration
- dry with materialThe chloroform solution (filtrate) was dried over magnesium sulphate
- concentrationconcentrated
- customto give a yellow oil which
- customon purification
Sources & evidence
- ORD record
- ord-6341669658d448d090460a5fc7fbfcdf
- Source dataset
- uspto-grants-1981_08
- Patent number
- US04284641
Reaction notes
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