Dimethylcarbamoyl Chloride → HCID 17838728, compound

HRID 1293127Notes

Reaction equation

HRID 1293127 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10][C:11]1[N:15]=[CH:14][NH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][N:23]([CH3:27])[C:24](Cl)=[O:25]>CN(C)C=O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[S:10][C:11]1[N:15]=[CH:14][N:13]([C:24](=[O:25])[N:23]([CH3:27])[CH3:22])[N:12]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 178425938HCID 178425938, compound

Product 1

HCID 17838728HCID 17838728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2,4,6-trimethylphenyl)thio-1H-1,2,4-triazole (220 mg), anhydrous potassium carbonate (280 mg) and N,N-dimethylformamide (1 ml) was added N,N-dimethylcarbamoyl chloride (0.14 ml), and the reaction mixture 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 subjected to a silica-gel column chromatography with 10 to 15% (20% 2-propanol/ethyl acetate)/hexane to yield the title compound (276 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

Sources & evidence

ORD record
ord-020e3345ccb04734a821f1bafead214f
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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