Ammonia → HCID 21421755, compound

HRID 1730043Notes

Reaction equation

HRID 1730043 reaction equation
N.O.S[C:4]1[N:5]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16]C=2)[C:6]([C:9]([NH2:11])=[O:10])=[CH:7][N:8]=1.[CH2:20](O)C>[Ni]>[C:13]1([CH:12]([N:5]2[C:6]([C:9]([NH2:11])=[O:10])=[CH:7][N:8]=[CH:4]2)[CH3:20])[CH:14]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 178513758HCID 178513758, compound

Product 1

HCID 21421755HCID 21421755, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To 80 parts of ethanol, previously saturated with gaseous ammonia, are added 2.3 parts of (-)-2-mercapto-1-(2-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 and 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 and eluent
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated

Sources & evidence

ORD record
ord-723dc4c2eb7040ffb2b8ff581d839afd
Source dataset
uspto-grants-1976_11
Patent number
US03991072

Reaction notes

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