Hydrogen Peroxide → 2,2′-Dithiobis[8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine]

HRID 374585Notes

Reaction equation

HRID 374585 reaction equation
[F:1][C:2]1[C:3]2[N:4]([NH:10][C:11](=[S:13])[N:12]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.OO>CO>[F:1][C:2]1[C:3]2[N:4]([N:10]=[C:11]([S:13][S:13][C:11]3[N:12]=[C:3]4[N:4]([C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]4[F:1])[N:10]=3)[N:12]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 15790247HCID 15790247, compound

Product 1

HCID 110584132,2′-Dithiobis[8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine]Yield 81.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
43 °C

Procedure

A heterogeneous mixture composed of 76.0 g (0.380 mol) of 8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c ]pyrimidine-2(3H)-thione and 400 g of methanol at 24° C. was prepared and 45.3 g (0.400 mol) of ice cold 30 percent by weight hydrogen peroxide solution was added with stirring. An exothermic reaction took place raising the temperature to 43° C. The mixture was allowed to react for about 75 min and then another 13.0 g (0,115 mol) of ice cold 30 percent by weight hydrogen peroxide solution was added with stirring. The mixture was allowed to react for another 30 m in and then the solids present were recovered by vacuum filtration. These solids were dried and were then slurried with methanol. The slurry was heated to reflux, cooled to 35°-45° C., and filtered to recover the insoluble solids. The solids were dried under reduced pressure at 40° C. to obtain 61.9 g of the title compound (80 percent of theory) as an off-white solid. The compound is a white powder melting at 201°-208° C. (dec.).

Workup

  1. customwas prepared
  2. customAn exothermic reaction
  3. customto react for about 75 min
  4. stirringwith stirring
  5. customto react for another 30 m in and then the solids
  6. filtrationpresent were recovered by vacuum filtration
  7. customThese solids were dried
  8. temperatureThe slurry was heated
  9. temperatureto reflux
  10. temperaturecooled to 35°-45° C.
  11. filtrationfiltered
  12. customto recover the insoluble solids
  13. customThe solids were dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-33e4d97cfa7746829eaa2eb520679aec
Source dataset
uspto-grants-1996_01
Patent number
US05480991

Reaction notes

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