Acetic Acid → 2-Benzylthio-8-chloro-5-methoxy[1,2,4]triazolo[1,5-a]pyridine

HRID 963161Notes

Reaction equation

HRID 963161 reaction equation
[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13]([Cl:18])=[CH:14][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>CO>[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13]([Cl:18])=[CH:14][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

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 190807452-Benzylthio-5,8-dichloro[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 190807292-Benzylthio-8-chloro-5-methoxy[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Benzylthio-5,8-dichloro[1,2,4]triazolo[1,5-a]pyridine (6.0 g, 0.019 mol) and 25 percent sodium methoxide in methanol (26.5 mL, 6.3 g, 0.116 mol) were combined in methanol and the mixture was heated to reflux for 2 hours. The mixture was then cooled, acidified with acetic acid, and concentrated by evaporation under reduced pressure. The residue was dissolved in dichloromethane and the solution was washed with water and concentrated by evaporation under reduced pressure The residue was triturated with hexane and the resulting solids were collected by filtration and dried to obtain 5.76 g (99 percent of theory) of the title compound as a light tan powder melting at 90°-91° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated by evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthe solution was washed with water
  7. concentrationconcentrated by evaporation under reduced pressure The residue
  8. customwas triturated with hexane
  9. filtrationthe resulting solids were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-3030cb9ab14e4f88a0ef5d96db935672
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

Loading…