Imidazole → 1-[2-(3-methoxyphenyl)ethyl]-1H-imidazole

HRID 129462Notes

Reaction equation

HRID 129462 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2531301-(2-Chloroethyl)-3-methoxybenzene

Product 1

HCID 193715841-[2-(3-methoxyphenyl)ethyl]-1H-imidazoleYield 62.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 67 g of 1-(2-chloroethyl)-3-methoxybenzene, 53.1 g of 1H-imidazole, 99 g of sodium carbonate, 500 ml of 4-methyl-2-pentanone and a few crystals of potassium iodide was stirred for 48 hours at reflux temperature. After cooling, the reaction mixture was diluted with water and extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated and the residue was destilled (13.3 Pa; 160° C.), yielding 49.5 g (62.8%) of 1-[2-(3-methoxyphenyl)ethyl]-1H-imidazole (interm. 10).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionextracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. custom(13.3 Pa; 160° C.)

Sources & evidence

ORD record
ord-328ee2ec607e4ca4b7d96eed576d238c
Source dataset
uspto-grants-1995_11
Patent number
US05468743

Reaction notes

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