3,5-Dimethylpyrazole → 3-(3,5-Dimethylpyrazol-1-yl)sulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole

HRID 1293149Notes

Reaction equation

HRID 1293149 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.Cl[S:9]([C:12]1[N:16]=[CH:15][N:14]([C:17](=[O:21])[N:18]([CH3:20])[CH3:19])[N:13]=1)(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([S:9]([C:12]2[N:16]=[CH:15][N:14]([C:17](=[O:21])[N:18]([CH3:19])[CH3:20])[N:13]=2)(=[O:10])=[O:11])[N:3]=1

Participants

5

Reactant 3

HCID 62103,5-DimethylpyrazoleHCID 11430Potassium CarbonateHCID 178387483-chlorosulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole

Product 1

HCID 178387173-(3,5-Dimethylpyrazol-1-yl)sulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazoleYield 67.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3,5-dimethylpyrazole (100 mg), 3-chlorosulfonyl-1-dimethylcarbamoyl-1H-1,2,4-triazole (Example 54-a) (480 mg), anhydrous potassium carbonate (280 mg), and acetonitrile (1.5 ml) was heated and stirred for 2 hours on an oil bath at 50° C. The reaction solution was extracted with ethyl acetate-water. The organic layer was washed with saturated aqueous sodium chloride solution, and concentrated. The residue was subjected to a silica-gel column chromatography with 20 to 30% (20% 2-propanol/ethyl acetate)/hexane, and the title compound (210 mg) was obtained by crystallization in ethyl acetate-hexane.

Workup

  1. temperaturewas heated
  2. extractionThe reaction solution was extracted with ethyl acetate-water
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-adf774deeeae4b009ab5785e2157b93c
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

Loading…