Water → HCID 53642213, compound

HRID 2295827Notes

Reaction equation

HRID 2295827 reaction equation
O.[Cl:2][C:3]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[N:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8]>[Zn].C(O)(=O)C>[Cl:2][C:3]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:7](=[O:8])[NH:9][C:10](=[O:11])[CH2:12][NH:13]1

Participants

5

Reactant 2

HCID 962WaterHCID 34839542-[(2,4-Dichlorophenyl)methyl]-5-hydroxy-1,2,4-triazin-3(2H)-one

Product 1

HCID 53642213HCID 53642213, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Into a three-necked flask equipped with a mechanical stirrer and a condenser were placed 300 ml of water, and stirring was commenced. 3 g of 1-(2',4'-dichlorobenzyl)-6-aza uracil were added and after a fine suspension had been obtained, of 60 ml of glacial acetic acid was added to this suspension. 3.3 g of fine zinc powder was then added in small portions. After all materials had been added the mixture was vigorously stirred and refluxed for 24 hours. The completion of the reduction was verified by thin layer chromatography. The mixture was cooled and the precipitate thus formed was filtered off and redissolved in hot methanol. The undissolved material was filtered off and the methanol solution was cooled to yield 2-(2',4'-dichlorobenzyl)hexahydro-1,2,4-triazine-3,5 dione; m.p. 230°; yield 1.4 g (60%).

Workup

  1. customInto a three-necked flask equipped with a mechanical stirrer and a condenser
  2. additionwas added to this suspension
  3. additionAfter all materials had been added the mixture
  4. stirringwas vigorously stirred
  5. temperaturerefluxed for 24 hours
  6. temperatureThe mixture was cooled
  7. customthe precipitate thus formed
  8. filtrationwas filtered off
  9. dissolutionredissolved in hot methanol
  10. filtrationThe undissolved material was filtered off
  11. temperaturethe methanol solution was cooled

Sources & evidence

ORD record
ord-d1aee1b26e3042baba387c5a30f27eaf
Source dataset
uspto-grants-1984_01
Patent number
US04426522

Reaction notes

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