α-(2-Acetylhydrazinylidene)benzeneacetic acid hydrazide → Metamitron

HRID 1438873Notes

Reaction equation

HRID 1438873 reaction equation
[C:1]([NH:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([NH:9][NH2:10])=[O:8])(=O)[CH3:2]>C(O)C>[NH2:10][N:9]1[C:7](=[O:8])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5][N:4]=[C:1]1[CH3:2]

Participants

3

Reactant 1

HCID 92518α-(2-Acetylhydrazinylidene)benzeneacetic acid hydrazide

Product 1

HCID 38854MetamitronYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

175 g (0.8 mol) of phenylglyoxylic acid hydrazide-2-acetylhydrazone were dissolved in 2 liters of ethanol and the solution was heated to boil under reflux for 12 hours. After cooling, the product which had precipitated was filtered off. The mother liquor was partially freed from the solvent; on cooling, a further precipitate was obtained, which was also filtered off and well washed with water. The combined precipitates were dried. 123 g (76% of theory) of 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-(4H)-one of melting point 160°-163° C. were obtained.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. customthe product which had precipitated
  5. filtrationwas filtered off
  6. temperatureon cooling
  7. customa further precipitate was obtained
  8. filtrationwhich was also filtered off
  9. washwell washed with water
  10. customThe combined precipitates
  11. customwere dried

Sources & evidence

ORD record
ord-c5c3933913bb454cb9391e076d8b65e9
Source dataset
uspto-grants-1977_11
Patent number
US04057546

Reaction notes

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