Phosphorus oxychloride → HCID 13562764, compound

HRID 477525Notes

Reaction equation

HRID 477525 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10](O)[N:9]2[N:13]=[CH:14][N:15]=[C:8]2[N:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:10]1[N:9]2[N:13]=[CH:14][N:15]=[C:8]2[N:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469341HCID 178469341, compound

Product 1

HCID 13562764HCID 13562764, compound

Conditions

Temperature
60 °C

Procedure

A suspension of 5-ethoxycarbonyl-7-hydroxy-s-triazolo[1,5-a]pyrimidine (6.8 g) in 40 ml of phosphorus oxychloride was heated at 60° C. with stirring, the resultant clear, orange solution was further refluxed for one hour, excess phosphorus oxychloride was distilled off, the brown residue was dissolved in 100 ml of chloroform, and the solution was slowly added to 100 ml of water with stirring. The chloroform solution was separated, dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography, affording 4.6 g of the objective compound as colorless crystals.

Workup

  1. temperaturethe resultant clear, orange solution was further refluxed for one hour
  2. distillationexcess phosphorus oxychloride was distilled off
  3. dissolutionthe brown residue was dissolved in 100 ml of chloroform
  4. additionthe solution was slowly added to 100 ml of water
  5. stirringwith stirring
  6. customThe chloroform solution was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0edce3a9780149b8a02fca50a440d253
Source dataset
uspto-grants-1989_12
Patent number
US04888332

Reaction notes

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