HCID 178490797, compound → N-p-methoxybenzylimidazole

HRID 1607107Notes

Reaction equation

HRID 1607107 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2S)=[CH:5][CH:4]=1>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 178490797HCID 178490797, compound

Product 1

HCID 578587N-p-methoxybenzylimidazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 15.0 g (0.068 mole) of 1-(4-methoxybenzyl)-2-mercaptoimidazole and 80 g of Raney® nickel in 800 ml of ethanol was refluxed for 4 hr. The nickel was filtered off and the filtrate was evaporated. The residue was dissolved in 100 ml of 1N HCl and this solution was washed with diethyl ether. The aqueous layer was basified with NaHCO3 and extracted with ethyl acetate. The extracts were dried (K2CO3) and filtered and the solvent was evaporated, to give 1-(4-methoxybenzyl)imidazole as an oil, 8.7 g (68%). A solution of this oil in acetone was treated with hexamic acid and diethyl ether, and the hexamate salt was crystallized, mp 157°-159°.

Workup

  1. temperaturewas refluxed for 4 hr
  2. filtrationThe nickel was filtered off
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in 100 ml of 1N HCl
  5. washthis solution was washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extracts were dried (K2CO3)
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b5d88334252449d0a84e0f98a6121216
Source dataset
uspto-grants-1989_09
Patent number
US04863944

Reaction notes

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