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

HRID 1723121Notes

Reaction equation

HRID 1723121 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CS(O[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH3:12])(=O)=O>C(#N)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH:11]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH3:12])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 112187991-(4-Nitrophenyl)ethyl methanesulfonate

Product 1

HCID 200265621-[1-(4-nitrophenyl)ethyl]-1H-imidazoleYield 63.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(a-2) A mixture of 37.5 parts of 1H-imidazole, 61.3 parts of [1-(4-nitrophenyl)ethyl] methanesulfonate and 200 parts of acetonitrile was stirred and refluxed for 2.50 hours. After cooling, the whole was filtered and the filtrate was evaporated. 150 Parts of water were added and the product was extracted three times with 130 parts of dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 34.4 parts (63.3%) of 1-[1-(4-nitrophenyl)ethyl]-1H-imidazole as a solid residue (int. 113).

Workup

  1. temperaturerefluxed for 2.50 hours
  2. temperatureAfter cooling
  3. filtrationthe whole was filtered
  4. customthe filtrate was evaporated
  5. addition150 Parts of water were added
  6. extractionthe product was extracted three times with 130 parts of dichloromethane
  7. customThe combined extracts were dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated

Sources & evidence

ORD record
ord-4755b98b0b424317ab3d63dff308126c
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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