Thionyl Chloride → 2-chloro-N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}benzenesulfonamide

Participants

Reaction Steps

2-chloro-N-{3-[4-(hydroxymethyl)phenyl]pyrazin-2-yl}benzene sulfonamide (3.15 g; 8.4 mmol; 1.00 eq.) was dissolved in dichloromethane (80 mL) and thionyl chloride (8.5 mL, 117 mmol, 14 eq.) was added dropwise. The reaction mixture was stirred overnight. The reaction mixture was poured carefully into ice/water (200 mL) and stirred until clear layers were formed. The mixture was separated and the organic layer was dried over MgSO4 and evaporated down to give the crude solid which was recrystallised in AcOEt/cyclohexane to give the pure 2-chloro-N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}benzenesulfonamide as a white solid (3.02 g, 95% yield, 99% HPLC purity).

Provenance & Evidence