Imidazole → 1-[4-(4-Methoxy-phenyl)-butyl]-1H-imidazole

HRID 1768036Notes

Reaction equation

HRID 1768036 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.[I-].[K+].[OH-].[Na+]>CC(O)(CC)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 5781911-(4-Bromobutyl)-4-methoxybenzene

Product 1

HCID 236145331-[4-(4-Methoxy-phenyl)-butyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 3.65 g (15.0 mmol) 1-(4-bromo-butyl)-4-methoxy-benzene, 1.02 g (15.0 mmol) imidazole, 2.74 g (16.5 mmol) potassium iodide, 0.60 g (15.0 mmol) sodium hydroxide and 20 ml 2-methyl-2-butanol was heated to reflux for 7 h. Solvents were distilled off, the residue dissolved in ethyl acetate and washed with water. Drying over Na2SO4 and removal of solvents in vacuo gave 2.0 g (58%) slightly colored oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 h
  3. distillationSolvents were distilled off
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialDrying over Na2SO4 and removal of solvents in vacuo
  7. customgave 2.0 g (58%) slightly colored oil

Sources & evidence

ORD record
ord-fa5c1b9344be421699bad692f75ddf8f
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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