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

HRID 1018502Notes

Reaction equation

HRID 1018502 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 44.4%

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. The reaction mixture is stirred at room temperature under nitrogen overnight. The reaction mixture is then 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 eluant to give 2.67 g (0.012 mol, 44%) of 1-(2-chlorobenzyl)-4,5-dimethylimidazole as a pale yellow oil. LC-MS (M++1): 221.2; 1H-NMR (δ, CDCl3): 2.00 (3H, s), 2.20 (3H, s), 5.07 (2H, s), 6.59 (1H, dd, J=9.2, 2), 7.17 (1H, td, J=8, 1.2), 7.23 (1H, td, J=8, 1.6), 7.38 (2H, dd, J=7.2, 1.6).

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-bf2db2a582764a24b66d0e6d733c41b3
Source dataset
uspto-grants-2002_11
Patent number
US06482844B1

Reaction notes

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