Ammonium Hydroxide → 1-Butyl-5-(4-methoxyphenyl)-1H-imidazole

HRID 1446842Notes

Reaction equation

HRID 1446842 reaction equation
Cl.[CH2:2]([N:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:9][N:8]=[C:7]1SC)[CH2:3][CH2:4][CH3:5].[OH-].[NH4+]>[Ni].CO>[CH2:2]([N:6]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[CH:9][N:8]=[CH:7]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 12833675HCID 12833675, compound

Product 1

HCID 202717331-Butyl-5-(4-methoxyphenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 11 parts of 1-butyl-5-(4-methoxyphenyl)-2-(methylthio)-1H-imidazole monohydrochloride, 20 parts of Raney-nickel catalyst, 105 parts of ammonium hydroxide and 8 parts of methanol is stirred for 2 hours at room temperature. The Raney-nickel catalyst is filtered off and another 20 parts of Raney-nickel catalyst is added. The whole is stirred for another 2 hours at room temperature. The catalyst is filtered off and the filtrate is evaporated. The residue is taken up in a small amount of water and the product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 8 parts of 1-butyl-5-(4-methoxyphenyl)-1H-imidazole as an oily residue.

Workup

  1. filtrationThe Raney-nickel catalyst is filtered off
  2. additionanother 20 parts of Raney-nickel catalyst is added
  3. stirringThe whole is stirred for another 2 hours at room temperature
  4. filtrationThe catalyst is filtered off
  5. customthe filtrate is evaporated
  6. extractionthe product is extracted with dichloromethane
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

Sources & evidence

ORD record
ord-b458cd18eaf74f1c94bbdea9be4b8f2d
Source dataset
uspto-grants-1982_02
Patent number
US04313953

Reaction notes

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