p-Toluenesulfonic acid → HCID 131710057, compound

HRID 1578926Notes

Reaction equation

HRID 1578926 reaction equation
[CH2:1]([C:3]1[N:8]([NH2:9])[C:7](=[O:10])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5][N:4]=1)[CH3:2].[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1>CC(C)=O>[CH2:1]([C:3]1[N:8]([N:9]=[CH:18][CH2:17][CH3:22])[C:7](=[O:10])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12323798HCID 12323798, compound

Product 1

HCID 131710057HCID 131710057, compoundYield 7,323.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.8 g (0.05 mole) of 3-ethyl-4-amino-6-phenyl-5H-1,2,4-triazin-5-one (known from DOS (German Published Specification) 2,138,031) were dissolved in 250 ml of acetone and after addition of 0.1 g of p-toluenesulphonic acid the mixture was heated to the boil under reflux for 1 hour. The reaction solution was filtered hot, the solvent was then partly distilled off and 20 to 50 ml of isopropanol were added to the residue. The crystalline precipitate thereupon obtained was filtered off and washed with ether. 10.9 g (85% of theory) of 3-ethyl-4-propylideneamino-6-phenyl-5-H-1,2,4-triazin-5-one of melting point 146°C were thus obtained.

Workup

  1. temperaturewas heated to the boil
  2. temperatureunder reflux for 1 hour
  3. filtrationThe reaction solution was filtered hot
  4. distillationthe solvent was then partly distilled off
  5. addition20 to 50 ml of isopropanol were added to the residue
  6. customThe crystalline precipitate thereupon obtained
  7. filtrationwas filtered off
  8. washwashed with ether

Sources & evidence

ORD record
ord-d8f79483f65747d591b15bf41338bde2
Source dataset
uspto-grants-1976_02
Patent number
US03940391

Reaction notes

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