Ammonia → HCID 21421755, compound

HRID 1730040Notes

Reaction equation

HRID 1730040 reaction equation
N.O.S[C:4]1[N:5]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:6]([C:9]([NH2:11])=[O:10])=[CH:7][N:8]=1>[Ni].C(O)C>[C:14]1([CH:12]([N:5]2[C:6]([C:9]([NH2:11])=[O:10])=[CH:7][N:8]=[CH:4]2)[CH3:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178436058HCID 178436058, compound

Product 1

HCID 21421755HCID 21421755, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 80 parts of ethanol, previously saturated with gaseous ammonia, are added 2.3 parts of (+)-2-mercapto-1-(1-phenylethyl)-1H-imidazole-5-carboxamide hydrate and 6 parts of Raney-nickel. The mixture is stirred and refluxed for 2 hours and thereafter allowed to cool to room temperature. The Raney-nickel is filtered off and the filter-cake is washed with ethanol. The filtrate is evaporated in vacuo and the residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding (+)-1-(1-phenylethyl)-1H-imidazole-5-carboxamide, essentially free of its (-)-isomer, as a residue.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe Raney-nickel is filtered off
  3. washthe filter-cake is washed with ethanol
  4. customThe filtrate is evaporated in vacuo
  5. customthe residue is purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and 5% of methanol as eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated

Sources & evidence

ORD record
ord-63f4a6ae6f3143bfb8f9c72308b0329b
Source dataset
uspto-grants-1976_11
Patent number
US03991072

Reaction notes

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