1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide → 3-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-chlorophenylmagnesium bromide (0.5 M in THF) (15.89 mL, 7.95 mmol) was added to a solution of 1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide (1.60 g, 6.11 mmol) in THF (20 mL) at −78° C. and under nitrogen. The mixture was stirred at −78° C. for 1 hour and then further stirred at room temperature for 5 hours. The mixture was quenched with NH4Cl (aq. sat. solution) and the product was extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield 3-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide (1.68 g, 88% yield) as a pale yellow solid.

Provenance & Evidence