Dimethyl Sulfoxide → 1-(4-Bromobenzyl)-1H-imidazole

HRID 1993859Notes

Reaction equation

HRID 1993859 reaction equation
CS(C)=O.[OH-].[K+].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>O>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 14797Potassium HydroxideHCID 685274-Bromobenzyl bromide

Product 1

HCID 29895571-(4-Bromobenzyl)-1H-imidazoleYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl sulphoxide (20 mL, dried over 4 Å molecular sieves) was added to potassium hydroxide (2.24 g, 0.04 mol, crushed pellets) and the mixture was stirred for 5 min. Imidazole (0.5718 g, 0.0084 mol) was then added and the mixture was stirred for 2 hours. 4-Bromobenzyl bromide (3.25 g, 0.013 mol) was added and the mixture was cooled briefly and stirred for a further hour before adding water (20 mL). The mixture was extracted with ether (3×100 mL) and each extract was washed with water (3×50 mL). The combined ether layers were dried over CaCl2 and the solvent was removed in vacuo. The residue was chromatographed on silica gel with CHCl3/MeOH (30:1) plus 0.05% formic acid as eluent yielding the sub-title compound (1.275 g, yield: 53%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. temperaturethe mixture was cooled briefly
  3. stirringstirred for a further hour
  4. extractionThe mixture was extracted with ether (3×100 mL)
  5. washeach extract was washed with water (3×50 mL)
  6. dry with materialThe combined ether layers were dried over CaCl2
  7. customthe solvent was removed in vacuo
  8. customThe residue was chromatographed on silica gel with CHCl3/MeOH (30:1) plus 0.05% formic acid as eluent

Sources & evidence

ORD record
ord-f1e99d34e6bb4a3586c8030a4698be9b
Source dataset
uspto-grants-2010_01
Patent number
US07652054B2

Reaction notes

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