Imidazole → 1-[2-(4-methylphenyl)ethyl]-1H-imidazole

HRID 129461Notes

Reaction equation

HRID 129461 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=O)=O.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 12942077HCID 12942077, compound

Product 1

HCID 110305321-[2-(4-methylphenyl)ethyl]-1H-imidazoleYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 28.9 g of 2-(4-methylphenyl)ethanol methanesulfonate, 18.6 g of 1H-imidazole, 22.7 g of potassium carbonate and 600 ml of tetrahydrofuran was stirred for 18 hours at reflux temperature. After cooling, the reaction mixture was evaporated and the residue was taken up in water and extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated and the residue was destilled (13.3 Pa; 120° C.), yielding 20.1 g (83.0%) of 1-[2-(4-methylphenyl)ethyl]-1H-imidazole (interm. 6).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. extractionextracted with 4-methyl-2-pentanone
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. custom(13.3 Pa; 120° C.)

Sources & evidence

ORD record
ord-f5becf5be765473c9021c08a83365753
Source dataset
uspto-grants-1995_11
Patent number
US05468743

Reaction notes

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