Chlorosulfonic acid → 3-(Ethoxycarbonyl)-1-methyl-5-phenyl-1H-pyrazole-4-sulfonic acid
Reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[CH2:6]([O:8][C:9]([C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]([CH3:22])[N:12]=1)=[O:10])[CH3:7]>C(Cl)(Cl)Cl>[CH2:6]([O:8][C:9]([C:11]1[C:15]([S:2]([OH:5])(=[O:4])=[O:3])=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:13]([CH3:22])[N:12]=1)=[O:10])[CH3:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 7.5 ml of chlorosulfonic acid and 15 xl of dry chloroform was cooled to 0° C., and a solution of 11.5 g (0.05 mol) of 3-ethoxycarbonyl-1-methyl5-phenylpyrazole in 25 ml of dry chloroform was added dropwise thereinto. Then, the mixture was stirred at room temperature for one hour and under reflux for 3 hours. After the reaction, by evaporation of chloroform, there was obtained oily 3-ethoxycarbonyl-1-methyl-5-phenylpyrazole-4-sulfonic acid. As the next step, at room temperature 20.9 g of phosphorus pentachloride was added portionwise, followed by stirring at 90° to 100° C. for one hour. The reaction mixture was added into ice-water and extracted with ether to obtain 14.7 g of 3-ethoxycarbonyl-1-methyl-5-phenylpyrazole-4-sulfonylchloride. Then, the resultant sulfonylchloride was dissolved in 20 ml of acetone and 4.48 g of KHCO was added to the solution. After a solution of 2.7 g of aqueous ammonia (28 %) and 6.5 ml of acetone was added dropwise thereinto at room temperature, the mixture was heated at 50 to 60 ° C. for 30 minutes. After evaporation of acetone, water was added to the residue, whereby 12.9 g of the title compound was precipitated as a solid. Recrystallization from benzene gave 8.4 g of the product. m.p. 141°-144° C.
Workup
- temperatureunder reflux for 3 hours
- customAfter the reaction
- customby evaporation of chloroform
Sources & evidence
- ORD record
- ord-7bcbe5ed5ce449ef88d04d163f269373
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04954164
Reaction notes
Loading…