Hydrochloric Acid → 2-Fluoro-4-({[2-(4-fluorophenoxy)-2-methylpropyl]amino}carbonyl)benzenesulfonyl chloride

Participants

Reaction Steps

4-Amino-3-fluoro-N-[2-(4-fluorophenoxy)-2-methylpropyl]benzamide (Preparation 94, 441 mg, 1.24 mmol) in 6 M of HCl in water (2 mL) was cooled at −5° C. Sodium nitrite (94.0 mg, 1.36 mmol) in water (0.5 mL, 30 mmol) was added slowly. After 20 minutes, sulfur dioxide in AcOH (8:25, sulfur dioxide:AcOH, 3 mL) and copper(II) chloride dihydrate (0.21 g, 1.2 mmol) were added to the reaction mixture. Vigorous gas evolution occurred. After 2 hours, the reaction was poured onto ice and water. The resulting solid was collected by filtration and washed with water and dried to afford a dark brown solid.

Provenance & Evidence