Methanol → HCID 19080750, compound

HRID 1940911Notes

Reaction equation

HRID 1940911 reaction equation
[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13]([Br: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.[CH3:20][O-:21].[Na+].CO>C(O)(=O)C>[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13]([Br:18])=[CH:14][CH:15]=[C:16]([O:21][CH3:20])[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 887Methanol2×HCID 10942334Sodium MethoxideHCID 19080758HCID 19080758, compound

Product 1

HCID 19080750HCID 19080750, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Benzylthio-8-bromo-5-chloro[1,2,4]triazolo[1,5-a]pyridine (7.7 g, 0.0217 mol) and 25 percent sodium methoxide in methanol (19.9 mL, 4.7 g, 0.0868 mol) were mixed with 400 mL of methanol and the mixture was heated to reflux for 1.5 hours. It was then cooled and acidified with acetic acid. The volatiles were removed by evaporation under reduced pressure and the residue was dissolved in dichloromethane. The resulting solution was washed with water and concentrated by evaporation under reduced pressure. The resulting residue was triturated with hexane and the solids obtained were recovered by filtration and dried to obtain 7.3 g (96 percent of theory) of the title compound as a light tan powder melting at 78°-79° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureIt was then cooled
  4. customThe volatiles were removed by evaporation under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washThe resulting solution was washed with water
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe resulting residue was triturated with hexane
  9. customthe solids obtained
  10. filtrationwere recovered by filtration
  11. customdried

Sources & evidence

ORD record
ord-6ff89886835e4577af1eb02374ae9a13
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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