6-Phenyl-1,2,4-triazine 4-oxide → 6-Phenyl-1,2,4-triazine

HRID 396149Notes

Reaction equation

HRID 396149 reaction equation
[C:1]1([C:7]2[N:12]=[N:11][CH:10]=[N+:9]([O-])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>P(OCC)(OCC)OCC>[C:1]1([C:7]2[N:12]=[N:11][CH:10]=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 64049796-Phenyl-1,2,4-triazine 4-oxide

Product 1

HCID 122539936-Phenyl-1,2,4-triazineYield 78%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Procedure

A mixture of 6-phenyl-[1,2,4]triazine-4-oxide (27 g, 156 mmol) and triethyl phosphite (500 ml) was heated under reflux for 30 min. The cooled reaction mixture was evaporated tit vacuo and the residue was purified by flash chromatography (SiO2; 50% Et2O in hexanes) to afford 19 g (121 mmol, 78%) of 6-phenyl-[1,2,4]triazine as a yellow solid. δH (400 MHz; CDCl3) 7.56-7.59 (3H, m, aromatics), 8.10-8.14 (2H, m, aromatics), 9.03 (1H, s, triazine H5), 9.65 (1H, s, triazine H3); m/z (ES+) 158 (M++H, 100%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. customThe cooled reaction mixture
  4. customwas evaporated tit vacuo
  5. customthe residue was purified by flash chromatography (SiO2; 50% Et2O in hexanes)

Sources & evidence

ORD record
ord-fbc5a481b1dd4530a51cb686e519bef6
Source dataset
uspto-grants-2003_08
Patent number
US06608062B1

Reaction notes

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