Dimethylcarbamoyl Chloride → HCID 17838721, compound

HRID 1293145Notes

Reaction equation

HRID 1293145 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([S:8][C:9]2[N:13]=[CH:12][NH:11][N:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:14][N:15]([CH3:19])[C:16](Cl)=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]([S:8][C:9]2[N:13]=[CH:12][N:11]([C:16](=[O:17])[N:15]([CH3:19])[CH3:14])[N:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 178419394HCID 178419394, compound

Product 1

HCID 17838721HCID 17838721, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(6-bromo-2-pyridyl)thio-1H-1,2,4-triazole (73 mg), dimethylcarbamoyl chloride (40 μl), anhydrous potassium carbonate (80 mg) and N,N-dimethylformamide (0.5 ml) was stirred at room temperature for 2 hours. 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 20% (20% 2-propanol/ethyl acetate)/hexane to yield the title compound (77 mg).

Workup

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

Sources & evidence

ORD record
ord-ec1ab3259db74d7a9535060fd20abc18
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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