Phosphorus oxychloride → HCID 19975238, compound

HRID 1450148Notes

Reaction equation

HRID 1450148 reaction equation
[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13](O)=[N:14][CH:15]=[C:16]([Br:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O>C(#N)C>[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13]([Cl:22])=[N:14][CH:15]=[C:16]([Br:17])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517599HCID 178517599, compound

Product 1

HCID 19975238HCID 19975238, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.04 g (3.08 mmol) of crude 2 -benzylthio-5-bromo-8 -hydroxy[1,2,4]triazolo[1,5 -a]pyrazine in 40 mL of dry acetonitrile was prepared in a flask equipped with a condenser and a drying tube and to this was added with stirring 4.0mL (43mmol) of phosphorus oxychloride. The mixture was heated at reflux for 3 hours and the solvent was then removed by evaporation under reduced pressure. The dark residue was dissolved in dichloromethane and the resulting solution was washed with water and dried over sodium sulfate. The residue obtained after removal of the solvent by evaporation under reduced pressure was purified by flash column chromatography on silica gel using dichloromethane as the eluent to obtain 0.26 g (24 percent of theory) of the title compound as an off-white solid melting at 109°-110° C.

Workup

  1. customwas prepared in a flask
  2. customequipped with a condenser and a drying tube
  3. additionto this was added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 3 hours
  6. customthe solvent was then removed by evaporation under reduced pressure
  7. dissolutionThe dark residue was dissolved in dichloromethane
  8. washthe resulting solution was washed with water
  9. dry with materialdried over sodium sulfate
  10. customThe residue obtained
  11. customafter removal of the solvent
  12. customby evaporation under reduced pressure
  13. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b8610ae1ce1742699eb54ca6a760b6bd
Source dataset
uspto-grants-1997_02
Patent number
US05602075

Reaction notes

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