Acetic Acid → HCID 19080731, compound

HRID 1940908Notes

Reaction equation

HRID 1940908 reaction equation
[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13](Br)=[CH:14][C:15]([Br:17])=[CH:16][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.C[O-].[Na+].[C:26](O)(=[O:28])C>O>[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[C:13]([O:28][CH3:26])=[CH:14][C:15]([Br:17])=[CH:16][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 10942334Sodium MethoxideHCID 19080744HCID 19080744, compound

Product 1

HCID 19080731HCID 19080731, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Benzylthio-6,8-dibromo[1,2,4]triazolo[1,5-a]pyridine (9.5 g, 23.8 mmol) was mixed with acetonitrile (50 mL) in a round bottom flask. Sodium methoxide (13.1 mL of 25 percent solution in methanol, 57.1 mmol) was added and the mixture was heated at reflux for 2 hours. Glacial acetic acid (10 mL) was added and the entire reaction mixture was poured into a mixture of ice and water (300 mL). The brown precipitate that formed was recovered by filtration and dried. This was chromatographed on silica gel eluting with a 1:1 mixture of ethyl acetate and hexane. Product-containing fractions were combined and concentrated under reduced pressure to obtain 6.58 g (80 percent of theory) of the title compound as a pale yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe entire reaction mixture
  4. customThe brown precipitate that formed
  5. filtrationwas recovered by filtration
  6. customdried
  7. customThis was chromatographed on silica gel eluting with a 1:1 mixture of ethyl acetate and hexane
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dde015bbbe8e4b8c945a8954f420872d
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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