Acetic Acid → 5-Methyl-2-methylsulfanyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 653570Notes

Reaction equation

HRID 653570 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[N:10]=[C:9]([S:11][CH3:12])[NH:8][N:7]=1.[C:13]([CH2:21][C:22](=O)[CH3:23])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)CCC>[CH3:23][C:22]1[CH:21]=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]2[N:8]=[C:9]([S:11][CH3:12])[N:10]=[C:6]2[N:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7166BenzoylacetoneHCID 178503514HCID 178503514, compound

Product 1

HCID 12558015-Methyl-2-methylsulfanyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 27.2%

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Procedure

To 50 ml of stirring glacial acetic acid, 2.5 g (19.2 mmol) of 3-amino-5-methylthio-1,2,4-triazole and 3.1 g (19.1 mmol) of benzoylacetone was added followed by heating at reflux for 2 h. 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 oil. Addition of n-butyl chloride resulted in crystallization of a solid which was filtered and washed with n-butyl chloride to give 1.33 g of the pure title compound, m.p. 121°-123° C.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 2 h
  3. customThe solvent was evaporated in vacuo and excess water
  4. additionadded to the residue
  5. extractionfollowed by extraction with 200 ml of ethyl acetate
  6. washThe extract was washed with water, saturated sodium bicarbonate, brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give an oil
  10. customresulted in crystallization of a solid which
  11. filtrationwas filtered
  12. washwashed with n-butyl chloride

Sources & evidence

ORD record
ord-e376680b4efa41c9b2eae7a05bfd0d1b
Source dataset
uspto-grants-1992_07
Patent number
US05127936

Reaction notes

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