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

HRID 2210986Notes

Reaction equation

HRID 2210986 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 min 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 min
  6. filtrationthe solids present 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-f96f035ed034426b9be7529fb452fc77
Source dataset
uspto-grants-1995_10
Patent number
US05461153

Reaction notes

Loading…