Phosphorus oxychloride → 7-Chloro-5-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidine

HRID 1707065Notes

Reaction equation

HRID 1707065 reaction equation
O[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:3]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515579HCID 178515579, compound

Product 1

HCID 203333567-Chloro-5-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidine

Procedure

A mixture of 3.50 g. of 7-hydroxy-5-(m-trifluoromethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine and 25 ml. of phosphorus oxychloride is refluxed for 6 hours. The excess reagent is removed by evaporation; ice is added and 1 N sodium hydroxide is added until the aqueous phase is basic to indicator paper. The compound is extracted with methylene chloride and the solution passed through a short column of a hydrous magnesium silicate. Evaporation of eluent gives the desired compound as a light yellow solid.

Workup

  1. additionA mixture of 3.50 g
  2. customThe excess reagent is removed by evaporation
  3. additionice is added
  4. addition1 N sodium hydroxide is added until the aqueous phase
  5. extractionThe compound is extracted with methylene chloride
  6. customEvaporation of eluent

Sources & evidence

ORD record
ord-f78e7b2fdd19449a8d8c6369f6c27a04
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

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