Trifluoroacetic acid → 5-Methyl-7-phenyl-2-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine

HRID 653569Notes

Reaction equation

HRID 653569 reaction equation
C(=O)(O)O.NNC(N)=N.FC(F)(F)C(O)=O.[NH2:17][C:18]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[NH:20][N:19]=1.[C:27]([CH2:35][C:36](=O)[CH3:37])(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl.C(O)(=O)C.C1(C)C=CC=CC=1>[NH2:17][C:18]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[NH:20][N:19]=1.[CH3:37][C:36]1[CH:35]=[C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:19]2[N:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=[C:18]2[N:17]=1

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7166BenzoylacetoneHCID 3508265-(trifluoromethyl)-4H-1,2,4-triazol-3-amineHCID 178513185HCID 178513185, compound

Product 2

HCID 3508265-(trifluoromethyl)-4H-1,2,4-triazol-3-amineHCID 27536745-Methyl-7-phenyl-2-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidineYield 112.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

By the procedure reported by V. A. Lopyrev Zh. Obshch. Khim. 53 p. 1684, 1983 (Chemical Abstracts 139865y, 1983) a crude sample of 3-amino-5-trifluoromethyl-1,2,4-triazole was prepared by the cyclocondensation of aminoguanidine bicarbonate with trifluoroacetic acid in refluxing toluene. This material was used effectively without further purification in subsequent ring condensation reactions. To 30 ml. of glacial acetic acid stirring, 3.0 g (19.7 mmol) of 3-amino-5-trifluoromethyl-1,2,4-triazole and 3.5 g (21.6 mmol) of benzoylacetone were added and the mixture heated at reflux for 3 h. A solution soon formed after heating. The solvent was evaporated in vacuo and excess water added to the residue followed by extraction with 200 ml of ethyl acetate. The extract was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and evaporated in vacuo to give an oily residue. Silica gel column chromatography (methylene chloride) afforded 3.09 g of the title compound which was present as the major component, m.p. 106°-108° C.

Workup

  1. customThis material was used effectively without further purification in subsequent ring condensation reactions
  2. temperaturethe mixture heated
  3. temperatureat reflux for 3 h
  4. customA solution soon formed
  5. temperatureafter heating
  6. customThe solvent was evaporated in vacuo and excess water
  7. additionadded to the residue
  8. extractionfollowed by extraction with 200 ml of ethyl acetate
  9. washThe extract was washed with water, saturated sodium bicarbonate, brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated in vacuo
  12. customto give an oily residue

Sources & evidence

ORD record
ord-ab63506cf30c49d6968d37c95c94bb80
Source dataset
uspto-grants-1992_07
Patent number
US05127936

Reaction notes

Loading…