Ethanol → 1-(4-methoxyphenyl)-5-phenyl-1H-imidazole

HRID 1389492Notes

Reaction equation

HRID 1389492 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][N:11]=[C:10]2S)=[CH:5][CH:4]=1.C(O)C.[OH-].[NH4+]>[Ni].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][N:11]=[CH:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 178491933HCID 178491933, compound

Product 1

HCID 130198821-(4-methoxyphenyl)-5-phenyl-1H-imidazoleYield 61%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 12 parts of 1-(4-methoxyphenyl)-5-phenyl-1H-imidazole-2-thiol, 10 parts of Raney-nickel catalyst, 160 parts of ethanol, 180 parts of ethyl acetate and 36 parts of ammonium hydroxide is stirred and refluxed overnight. The solution is decanted and the residual Raney-nickel is boiled again in a mixture of 160 parts of ethanol and 180 parts of ethyl acetate. The solvent is decanted. The combined ethanol/ethyl acetate phases are evaporated. The residue is crystallized from a mixture of 2-propanol and water. The product is filtered off and dried, yielding 6.5 parts (61%) of 1-(4-methoxyphenyl)-5-phenyl-1H-imidazole; mp. 105.7° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe solution is decanted
  3. additionthe residual Raney-nickel is boiled again in a mixture of 160 parts of ethanol and 180 parts of ethyl acetate
  4. customThe solvent is decanted
  5. customThe combined ethanol/ethyl acetate phases are evaporated
  6. customThe residue is crystallized from a mixture of 2-propanol and water
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-2ed083db719c4b27a22e0603863d844b
Source dataset
uspto-grants-1981_01
Patent number
US04244964

Reaction notes

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