Dimethylcarbamoyl Chloride → 3-(2-Methylimidazo[1,2-a]pyridin-3-yl)sulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole

HRID 1293143Notes

Reaction equation

HRID 1293143 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[S:11]([C:14]1[N:18]=[CH:17][NH:16][N:15]=1)(=[O:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>CN(C)C=O>[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1[S:11]([C:14]1[N:18]=[CH:17][N:16]([C:27](=[O:28])[N:26]([CH3:30])[CH3:25])[N:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 1784321633-(2-methylimidazo[1,2-a]pyridin-3-yl)sulfonyl-1H-1,2,4-triazole

Product 1

HCID 178387473-(2-Methylimidazo[1,2-a]pyridin-3-yl)sulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2-methylimidazo[1,2-a]pyridin-3-yl)sulfonyl-1H-1,2,4-triazole (100 mg), anhydrous potassium carbonate (105 mg) and N,N-dimethylformamide (0.5 ml) was added dimethylcarbamoyl chloride (0.06 ml), and the reaction mixture was stirred at room temperature overnight. The reaction solution was extracted with ethyl acetate-water. The organic layer was washed with water, followed by saturated aqueous sodium chloride solution, and concentrated. The residue was subjected to a silica-gel column chromatography with 30 to 50% (20% 2-propanol/ethyl acetate)/hexane to yield the title compound (107 mg).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate-water
  2. washThe organic layer was washed with water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b3d09093e73448ff8192feb358443693
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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