Acetic Acid → 2-Benzylthio-5-methoxy-7-methyl[1,2,4]triazolo[1,5-a]pyridine

HRID 963152Notes

Reaction equation

HRID 963152 reaction equation
[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16](Cl)[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[C:23](O)(=[O:25])C.CCCCCC>CO.ClCCl>[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([O:25][CH3:23])[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8058HexaneHCID 10942334Sodium MethoxideHCID 190807642-Benzylthio-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 190807762-Benzylthio-5-methoxy-7-methyl[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-benzylthio-5-chloro-7-methyl[1,2,4]triazolo[1,5-a]pyridine (5.0 g, 0.017 mol), sodium methoxide in methanol (16 mL of 25 percent, 3.7 g, 0.070 mol) and methanol (100 mL) were heated at reflux with stirring for 4 hours. The reaction mixture was then cooled, acidified with acetic acid (10 mL), and concentrated by evaporation under reduced pressure. The residue obtained was dissolved in dichloromethane and the resulting solution was washed well with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue obtained was mixed with hexane and filtered to recover the solids. The solids were dried to obtain 4.7 g (97 percent of theory) of the title compound as a tan powder melting at 85°-87° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue obtained
  6. washthe resulting solution was washed well with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe residue obtained
  10. filtrationfiltered
  11. customto recover the solids
  12. customThe solids were dried

Sources & evidence

ORD record
ord-d58cef6c58fb46d19d35f85904ceb81e
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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