Sodium Hydroxide → HCID 59846261, compound

Participants

Reaction Steps

NaOH (2 M aq, 0.91 mL, 1.8 mmol) was added to a solution of N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-formyl-benzenesulfonamide (305 mg, 1 mmol) and 1-(4-chloro-2-phenylamino-phenyl)-ethanone (250 mg, 1 mmol) in MeOH (10 mL), and the resulting mixture stirred at RT overnight. A second aliquot of NaOH (2 M aq, 0.1 mL) was added, and the reaction mixture was again stirred at RT overnight. The resulting mixture was evaporated under reduced pressure, and the crude residue partitioned between water and EtOAc. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give an oil. The crude residue was purified twice by flash chromatography (EtOAc/hexane) to give 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-N-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-benzenesulfonamide (70 mg).

Provenance & Evidence