Imidazole → 1-[3-(4-Nitrophenoxy)propyl]-1H-imidazole

HRID 1357551Notes

Reaction equation

HRID 1357551 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>O1CCOCC1>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 2611281-(3-bromopropoxy)-4-nitrobenzene

Product 1

HCID 132191281-[3-(4-Nitrophenoxy)propyl]-1H-imidazoleYield 35.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of imidazole (0.8 g, 11.6 mmol) and 4-(3-bromopropoxy)nitrobenzene (1.5 g, 5.8 mmol) in 1,4-dioxane (75 ml) was heated at 100° C. for 12 hours. Volatile material was removed by evaporation and the residue was dissolved in ethyl acetate (150 ml). The solution was washed with saturated sodium bicarbonate (3×50 ml), water (3×50 ml) and saturated sodium chloride (50 ml) and then dried. The solvent was removed by evaporation and the residue was purified by column chromatography, eluting with 0-5% methanol in DCM, to give the product as a yellow oil (0.51 g, 22%). MS (MH+): 248.

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate (150 ml)
  3. washThe solution was washed with saturated sodium bicarbonate (3×50 ml), water (3×50 ml) and saturated sodium chloride (50 ml)
  4. customdried
  5. customThe solvent was removed by evaporation
  6. customthe residue was purified by column chromatography
  7. washeluting with 0-5% methanol in DCM

Sources & evidence

ORD record
ord-a55ec05bd1be4a0c95e87cb8d1064df0
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

Loading…