HCID 11736048, compound → HCID 178454522, compound

HRID 1660542Notes

Reaction equation

HRID 1660542 reaction equation
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].[C:10]([NH:15][CH:16]([CH3:24])[C:17](=O)[C:18](OCC)=[O:19])(=[O:14])[CH2:11][CH2:12][CH3:13]>C(O)C>[NH2:8][C:7]1[NH:6][N:5]=[C:17]([CH:16]([NH:15][C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[CH3:24])[C:18](=[O:19])[N:9]=1

Participants

4

Reactant 2

HCID 11736048HCID 11736048, compoundHCID 178513185HCID 178513185, compound2×

Product 1

HCID 178454522HCID 178454522, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aminoguanidine bicarbonate (2.4 g) was suspended in a solution of ethyl 3-butyramido-2-oxo-butyrate (3.8 g) in absolute ethanol (40 ml) and the mixture was heated under reflux for 5 hours. During this period aminoguanidine bicarbonate gradually dissolved and a new product precipitated as a white solid. The mixture was cooled and the solid (2.62 g) collected and taken up in 2 N hydrochloric acid (30 ml). The solution was filtered to remove a small amount of undissolved solid, then adjusted to pH 8 by adding solid sodium carbonate. The triazinone separated as a white solid which was collected, washed with water and dried in vacuo at 100° to give material m.p. 308° (dec.), (2.0 g) (50% approx.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customa new product precipitated as a white solid
  4. temperatureThe mixture was cooled
  5. customthe solid (2.62 g) collected
  6. filtrationThe solution was filtered
  7. customto remove a small amount of undissolved solid
  8. additionby adding solid sodium carbonate
  9. customThe triazinone separated as a white solid which
  10. customwas collected
  11. washwashed with water
  12. customdried in vacuo at 100°

Sources & evidence

ORD record
ord-b61e293b24b64c52b37ef168200ec39b
Source dataset
uspto-grants-1981_12
Patent number
US04308384

Reaction notes

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