HCID 17838654, compound → HCID 25175693, compound

Participants

Reaction Conditions

Reaction Steps

4-(N-thiazol-2-ylsulfamoyl)benzene-1-sulfonyl chloride (0.339 g, 0.00100 mol) was mixed in tetrahydrofuran (15 mL) and cooled to −78° C. Phenylmagnesium bromide (0.363 g, 0.002 mol) solution in THF (1M) was added to the reaction in a dropwise manner. The reaction was allowed to stir 1 hour while warming to room temperature. A second portion of phenyl magnesium bromide solution (0.181 g, 0.001 mol) was added to the reaction mixture. The reaction mixture was then stirred for 18 hours then quenched with saturated ammonium chloride solution. The organic phase was separated and dried over magnesium sulfate. The organic phase was evaporated to a residue and purified by column chromatography (12 g silica gel ISCO column, hexanes to ethyl acetate gradient elution). Product fractions were combined and rotary evaporated to give 15.7 mg of product as white crystals. LCMS: Rt=1.30 min, MS m/z 380.6 [MH]+.

Provenance & Evidence