Phosphorus oxychloride → 5-tert-butyl-7-chloro[1,2,4]triazolo[1,5-a]pyrimidine

HRID 364004Notes

Reaction equation

HRID 364004 reaction equation
O[C:2]1[N:3]2[C:7]([N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[N:6][CH:5]=[N:4]2.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:2]1[N:3]2[C:7]([N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[N:6][CH:5]=[N:4]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178441199HCID 178441199, compound

Product 1

HCID 167682715-tert-butyl-7-chloro[1,2,4]triazolo[1,5-a]pyrimidine

Procedure

The mixture of 20 g of 4-hydroxy-6-t-butyl-1,3,3a,7-tetraazaindene and 80 ml of phosphorus oxychloride was refluxed over an oil bath at 140° to 150° C. for 3 to 4 hours. Excess phosphorus oxychloride was distilled away under reduced pressure and then the reaction mixture was poured into ice water. The product was extracted with methylene chloride, and dried over anhydrous sodium sulfate. Upon distilling off the methylene chloride, pale yellow crystal in yield of 16 g was obtained.

Workup

  1. temperaturewas refluxed over an oil bath at 140° to 150° C. for 3 to 4 hours
  2. distillationExcess phosphorus oxychloride was distilled away under reduced pressure
  3. additionthe reaction mixture was poured into ice water
  4. extractionThe product was extracted with methylene chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationUpon distilling off the methylene chloride, pale yellow crystal in yield of 16 g
  7. customwas obtained

Sources & evidence

ORD record
ord-cf357713a53148e0a0d4df72b049146b
Source dataset
uspto-grants-1986_08
Patent number
US04604339

Reaction notes

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