Acetic Acid → HCID 178513792, compound

HRID 1856188Notes

Reaction equation

HRID 1856188 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N+:6]([O-:9])=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+].N[CH:14]([C:18]([NH2:20])=[O:19])[C:15]([NH2:17])=[O:16].C(O)(=O)C>CO>[C:18]([C:14]1[N:2]=[C:1]([C:3]2[CH:8]=[CH:7][N+:6]([O-:9])=[CH:5][CH:4]=2)[NH:17][C:15]=1[OH:16])(=[O:19])[NH2:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 846844-Pyridinecarbonitrile, 1-oxideHCID 964572-AminopropanediamideHCID 10942334Sodium Methoxide

Product 1

HCID 178513792HCID 178513792, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-cyanopyridine N-oxide (600 g) in ahydrous methanol (250 ml) was added sodium methoxide (1.35 g), and this solution was stirred for 0.5 hour at room temperature. To this solution were added aminomalonamide (3.51 g) and acetic acid, and this mixture was stirred for 2 hours under reflux. After cooling the reaction mixture to 0°-5° C., the precipitated product was separated by filtration, washed with ethanol, isopropylether and dried under vacuum to give yellow crystal of 4-(4-carbamoyl-5-hydroxyimidazole-2yl)-pyridine-N-oxide (5.96 g).

Workup

  1. stirringthis mixture was stirred for 2 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling the reaction mixture to 0°-5° C.
  4. customthe precipitated product was separated by filtration
  5. washwashed with ethanol, isopropylether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d909f152f6744ec59324316f91b5ba83
Source dataset
uspto-grants-1980_08
Patent number
US04218457

Reaction notes

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