Phosphorus oxychloride → HCID 19989245, compound

HRID 477538Notes

Reaction equation

HRID 477538 reaction equation
[NH2:1][C:2]1[N:12]=[C:5]2[N:6]=[C:7]([CH3:11])[CH:8]=[C:9](O)[N:4]2[N:3]=1.P(Cl)(Cl)([Cl:15])=O>>[NH2:1][C:2]1[N:12]=[C:5]2[N:6]=[C:7]([CH3:11])[CH:8]=[C:9]([Cl:15])[N:4]2[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429176HCID 178429176, compound

Product 1

HCID 19989245HCID 19989245, compound

Procedure

2-Amino-7-hydroxy-5-methyl-s-triazolo[1,5-a]pyrimidine (20 g) was suspended in 120 ml of phosphorus oxychloride under ice cooling, and the suspension was refluxed for two hours. Excess phosphorus oxychloride was removed by distillation under normal pressure. The 40 ml of reddish brown oil left was shaken with 300 ml of dichloromethane and 200 ml of water and the organic layer was collected. The aqueous layer was again extracted with 200 ml of fresh dichloromethane, and the combined organic extract was treated with saturated sodium bicarbonate solution until the pH of washings rose to 7 to 8, then washed with 100 ml of saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the dried solution was concentrated under reduced pressure to about 30 ml, and the concentrate was crystallized using 80 ml of n-hexane, affording 17 g of the objective compound as faint yellow crystals.

Workup

  1. temperaturethe suspension was refluxed for two hours
  2. customExcess phosphorus oxychloride was removed by distillation under normal pressure
  3. waitThe 40 ml of reddish brown oil left
  4. customthe organic layer was collected
  5. extractionThe aqueous layer was again extracted with 200 ml of fresh dichloromethane
  6. extractionthe combined organic extract
  7. additionwas treated with saturated sodium bicarbonate solution until the pH of washings
  8. washwashed with 100 ml of saturated sodium chloride solution
  9. dry with materialAfter drying over anhydrous magnesium sulfate
  10. concentrationthe dried solution was concentrated under reduced pressure to about 30 ml
  11. customthe concentrate was crystallized

Sources & evidence

ORD record
ord-9422dda4606c40dc8c80ae11b4aec21a
Source dataset
uspto-grants-1989_12
Patent number
US04888332

Reaction notes

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