Acetic Acid → HCID 19080760, compound

HRID 1940913Notes

Reaction equation

HRID 1940913 reaction equation
[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[CH:13]=[C:14]([Br:18])[CH:15]=[C:16](Br)[N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].C(#N)C.[C:26](O)(=[O:28])C>CO>[CH2:1]([S:8][C:9]1[N:19]=[C:12]2[CH:13]=[C:14]([Br:18])[CH:15]=[C:16]([O:28][CH3:26])[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 Methoxide2×HCID 19080757HCID 19080757, compound

Product 1

HCID 19080760HCID 19080760, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Benzylthio-5,7-dibromo[1,2,4]triazolo[1,5-a]pyridine (11.6 g, 0.029 mol) and 25 percent sodium methoxide in methanol (13.0 mL, 3.1 g, 0.057 mol) were combined with 300 mL of acetonitrile and the mixture was heated to reflux with stirring for an hour. An additional 26 mL of 25 percent sodium methoxide in methanol was then added. After a 15-min reaction period, the mixture was acidified with acetic acid and the volatiles were removed by evaporation under reduced pressure. The residue was chromatographed on silica gel eluting with 20 percent ethyl acetate in hexane to obtain 4.97 g (49 percent of theory) of the title compound as a tan powder melting at 80°-82° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customAfter a 15-min reaction period
  4. customthe volatiles were removed by evaporation under reduced pressure
  5. customThe residue was chromatographed on silica gel eluting with 20 percent ethyl acetate in hexane

Sources & evidence

ORD record
ord-fece12db7b034759b0b3558cd023e549
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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