Potassium Carbonate → HCID 178419394, compound

HRID 1293144Notes

Reaction equation

HRID 1293144 reaction equation
[SH:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[N:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:7][C:8]1[N:9]=[C:10]([S:1][C:2]2[N:6]=[CH:5][NH:4][N:3]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 178527894HCID 178527894, compound

Product 1

HCID 178419394HCID 178419394, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-mercapto-1H-1,2,4-triazole (200 mg), 2,6-dibromopyridine (560 mg), anhydrous potassium carbonate (420 mg) and N,N-dimethylformamide (1 ml) was heated and stirred for 3 hours on an oil bath at 100° C. The reaction solution was extracted with ethyl acetate-water. The organic layer was washed with water, followed by saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a silica-gel column chromatography with 5 to 30% (20% 2-propanol/ethyl acetate)/hexane to yield the title compound (73 mg).

Workup

  1. temperaturewas heated
  2. extractionThe reaction solution was extracted with ethyl acetate-water
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica-gel column chromatography with 5 to 30% (20% 2-propanol/ethyl acetate)/hexane

Sources & evidence

ORD record
ord-2cf8c9055a2549a2979450a355b4eaf8
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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