Phenyl isocyanatoformate → 2,3-Dimethyl-3H-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-dione

HRID 889158Notes

Reaction equation

HRID 889158 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[C:3]1[NH2:8].[N:9]([C:12](OC1C=CC=CC=1)=[O:13])=[C:10]=[O:11]>C(#N)C>[CH3:7][C:6]1[N:2]([CH3:1])[C:3]2=[N:8][C:10](=[O:11])[NH:9][C:12](=[O:13])[N:4]2[N:5]=1

Participants

4

Reactant 2

HCID 4148962Phenyl isocyanatoformateHCID 122527104,5-Dimethyl-4H-1,2,4-triazol-3-amine

Product 1

HCID 579273132,3-Dimethyl-3H-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-dioneYield 138.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

After suspending 4,5-dimethyl-4H-[1,2,4]triazol-3-ylamine (CAS 53132-83-5) (7.6 g) in acetonitrile (80 ml), a solution of phenyl isocyanatoformate (5.2 g) in acetonitrile (40 ml) was slowly added dropwise while heating to reflux. After heating to reflux for 6 hours, the reaction mixture was cooled on ice. The insoluble matter was collected by filtration to obtain the title compound (7.98 g).

Workup

  1. temperaturewhile heating to reflux
  2. temperatureAfter heating
  3. temperatureto reflux for 6 hours
  4. temperaturethe reaction mixture was cooled on ice
  5. filtrationThe insoluble matter was collected by filtration

Sources & evidence

ORD record
ord-0008d401c5e64445ad1628fcb5573867
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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