Potassium Iodide → 2-{1-[4-(4-Methoxy-phenyl)-butyl]-1H-imidazol-2-yl}-ethanol

HRID 750944Notes

Reaction equation

HRID 750944 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]=[C:15]1[CH2:19][CH2:20][OH:21].[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]=[C:15]2[CH2:19][CH2:20][OH:21])=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 64052-Methyl-2-butanolHCID 14798Sodium HydroxideHCID 5781911-(4-Bromobutyl)-4-methoxybenzeneHCID 150160802-(1H-imidazol-2-yl)ethan-1-ol

Product 1

HCID 236145362-{1-[4-(4-Methoxy-phenyl)-butyl]-1H-imidazol-2-yl}-ethanol

Procedure

A mixture of 3.65 g (15.0 mmol) 1-(4-bromo-butyl)-4-methoxy-benzene, 2.52 g (22.5 mmol) 2-(1H-imidazol-2-yl)-ethanol, 2.74 g (16.5 mmol) potassium iodide, 0.90 g (22.5 mmol) sodium hydroxide and 15 ml 2-methyl-2-butanol was heated to reflux for 12 h. Solvents were distilled off, the residue dissolved in toluene and washed with water. After drying over Na2SO4 and removal of solvents in vacuo the residue was stirred with 7 ml ethyl acetate, isolated by filtration, washed with ethyl acetate and dried. Yield 2.41 g (59%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. distillationSolvents were distilled off
  4. dissolutionthe residue dissolved in toluene
  5. washwashed with water
  6. dry with materialAfter drying over Na2SO4 and removal of solvents in vacuo the residue
  7. customisolated by filtration
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-dadd22ed7c724975a3056582ede86a0d
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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