Imidazole → 1-(3-methoxy-benzyl)-1H-imidazole

HRID 900251Notes

Reaction equation

HRID 900251 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br>>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 122293911-(3-methoxy-benzyl)-1H-imidazoleYield 83.2%

Conditions

Temperature
5 °C

Procedure

To a solution of imidazole (1.00 g, 14.69 mmol, 1 equivalent) and Cs2CO3 (5.93 g, 1.2 equivalents) was added 3-methoxybenzyl bromide (3.24 g, 1.1 equiv.) dropwise at 5° C. The mixture was stirred for 1.5 h at 5° C., filtered and concentrated under reduced pressure to give 1-(3-methoxy-benzyl)-1H-imidazole (2.30 g) as a pale yellow oil was directly used in the next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02521878fd1b481baddc4e4d868fb484
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

Loading…