Phosphorus oxychloride → HCID 13562760, compound

HRID 973813Notes

Reaction equation

HRID 973813 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[N:10]([N:13]=[CH:14][N:15]=2)[C:11]=1O)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:11]1[N:10]2[N:13]=[CH:14][N:15]=[C:9]2[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469693HCID 178469693, compound

Product 1

HCID 13562760HCID 13562760, compound

Procedure

A suspension of 6-ethoxycarbonyl-7-hydroxy-s-triazolo[1,5-a]pyrimidine (7 g) in phosphorus oxychloride (20 ml) was refluxed for 30 minutes, the resultant orange solution was further refluxed for one hour, and excess phosphorus oxychloride was removed by distillation under reduced pressure. Benzene (50 ml) was added to the residue, and remaining phosphorus oxychloride was completely removed by azeotropic distillation under reduced pressure. Chloroform (80 ml) was added to the residue, the insoluble matters were filtered off, and the solvent was removed in vacuo from the filtrate. Purification of the brown residue by silica gel column chromatography gave 3.9 g of the objective compound as colorless crystals.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe resultant orange solution was further refluxed for one hour
  3. customexcess phosphorus oxychloride was removed by distillation under reduced pressure
  4. additionBenzene (50 ml) was added to the residue
  5. customwas completely removed by azeotropic distillation under reduced pressure
  6. additionChloroform (80 ml) was added to the residue
  7. filtrationthe insoluble matters were filtered off
  8. customthe solvent was removed in vacuo from the filtrate
  9. customPurification of the brown residue by silica gel column chromatography

Sources & evidence

ORD record
ord-42893d5a7392448bab5d1a17ea93846e
Source dataset
uspto-grants-1991_11
Patent number
US05064953

Reaction notes

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