Diethyl Ether → 1-[(2-Chlorophenyl)methyl]-4,5-dimethyl-1H-imidazole

HRID 1635573Notes

Reaction equation

HRID 1635573 reaction equation
Br.[CH3:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[CH3:8].[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12]Br.[OH-].[K+].CCOCC>CN(C=O)C.O>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][N:4]1[C:3]([CH3:2])=[C:7]([CH3:8])[N:6]=[CH:5]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11905alpha-Bromo-o-chlorotolueneHCID 14797Potassium HydroxideHCID 18676173HCID 18676173, compound

Product 1

HCID 120111831-[(2-Chlorophenyl)methyl]-4,5-dimethyl-1H-imidazoleYield 44.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.89 g (0.027 mol) of 4,5-dimethylimidazole hydrobromide and 5.7 g (0.028 mol) of 2-chlorobenzyl bromide in 20 ml of DMF is added 6 ml of 50% potassium hydroxide aqueous solution dropwise. Then the reaction mixture is stirred at RT under nitrogen overnight. The reaction mixture is poured into ether (100 ml)/ water (50 ml). The ether layer is separated, washed with water (10 ml×2), dried over anhydrous sodium sulfate and evaporated in vacuo. The raw material is subjected to chromatography on silica gel using dichloromethane-methanol (10:1) as eluent to give 2.67 g (44%) of 1-(2′-chlorobenzyl)-4,5-dimethylimidazole as a pale yellow oil. MS m/z (M++1) 221; 1H-NMR 400 MHz(δ, CDCl3): 2.00 (3H, s), 2.20 (3H, s), 5.07 (2H, s), 6.59 (1H, dd, J=9.2, 2 Hz), 7.17 (1H, td, J=8, 1.2 Hz), 7.23 (1H, td, J=8, 1.6 Hz), 7.38 (2H, dd, J=7.2, 1.6 Hz) ppm.

Workup

  1. customThe ether layer is separated
  2. washwashed with water (10 ml×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5131e08a8d4a47529f9e5e47e8cf73aa
Source dataset
uspto-grants-2003_01
Patent number
US06509366B2

Reaction notes

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