Thionyl Chloride → HCID 67131071, compound

Participants

Reaction Steps

2-Azido-N-(4-chloro-phenyl)-4,5-difluoro-benzamide (18.5 g, 60 mmol) was suspended in thionyl chloride (193 ml). The suspension was heated under reflux conditions for 14 h. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane. Under ice cooling saturated NaHCO3 solution was added until pH 8 was reached. The mixture was extracted two times with dichloromethane, the combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a brown solid which was crystallized from methanol/dichloromethane/n-heptane to give the title compound (16.8 g, 56 mmol; 94%) as off-white crystals. MS: m/e=299.5 [M+H+].

Provenance & Evidence