Water → 1-Dimethylsulfamoyl-1,2,4-triazole-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:18][N:19]([CH3:24])[S:20](Cl)(=[O:22])=[O:21].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:10]=[CH:9][N:8]([S:20](=[O:22])(=[O:21])[N:19]([CH3:24])[CH3:18])[N:7]=1)=[O:5])[CH3:2]Participants
Procedure
To a solution of 1.02 g (7.23 mmol) of 1H-1,2,4-triazole-3-carboxylic acid ethyl ester in 6 ml of DMF was added 1.46 g (1.44 mmol) of triethylamine. To the solution was added dropwise with stirring under ice-cooling 1.14 g (7.94 mmol) of dimethylsulfamoyl chloride. The mixture was stirred at room temperature for 8 hours. 30 ml of Water was added thereto and extracted with 20 ml of ethylacetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, dried over Na2SO4 and evaporated under reduced pressure to give an oil. The obtained oil was purified with silica gel chromatography (eluate: hexane/ethylacetate=2:1) to give 1.46 g of 1-dimethylsulfamoyl-1,2,4-triazole-3-carboxylic acid ethyl ester as a white crystal. Yield: 82%.
Workup
- additionTo the solution was added dropwise
- stirringThe mixture was stirred at room temperature for 8 hours
- extractionextracted with 20 ml of ethylacetate
- washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and water
- dry with materialdried over Na2SO4
- customevaporated under reduced pressure
- customto give an oil
- customThe obtained oil was purified with silica gel chromatography (eluate: hexane/ethylacetate=2:1)
Sources & evidence
- ORD record
- ord-e5bb0d53b8784ce3bd9e8f832d0bfc19
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06831177B1
Reaction notes
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