Ethanol → N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide

Participants

Reaction Steps

To N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-[(phenylmethyl)oxy]benzenesulfonamide (974 mg, 2.300 mmol) was added ammonium formate (725 mg, 11.50 mmol) palladium(II) hydroxide (20% on carbon) (164 mg, 0.230 mmol) and ethanol (65 mL). The reaction mixture was heated to reflux with stirring overnight. A product peak was observed by LCMS, but only partial conversion had occurred. A further 5 equivalents of ammonium formate (725 mg, 11.50 mmol) were added to the reaction mixture. The reaction mixture was reheated to boiling point. After a further 30 minutes of heating, LCMS showed no change in the ratio of starting material to product. The reaction was cooled for 5 minutes then additional palladium(II) hydroxide (20% on carbon) (164 mg, 0.230 mmol) was added. The reaction mixture was then reheated to reflux for another 30 minutes after which full conversion to the product was observed. The reaction mixture was cooled, filtered through a celite cartridge, then concentrated in vacuo to give 727 mg of crude product. The crude mixture was diluted with ethyl acetate and washed with water, then brine. The organic phase was then concentrated in vacuo to give 663 mg of the title compound. LCMS [LCMS1] Rt 1.25 min, m/z (ES+) 334 (M+H).

Provenance & Evidence