Hydrochloric Acid → HCID 18454316, compound

Participants

Reaction Steps

For their studies, p-Methylsulfonylaniline (1.42 g, 8.3 mmol) was sequentially treated with HCl (15 ml of a 6M solution, 9 mmol) and sodium nitrite (0.66 g, 9.12 mmol) while the temperature was maintained between 0–5° C. The reagents were allowed to dissolve and the resulting solution was allowed to stir for an about 15 minutes. The resulting diazonium compound was then treated with m-toluidine (0.9 g, 8.4 mmol) in THF, and allowed to stir for about 15 minutes to 1 h. To the resulting red-orange mixture was added sodium acetate NaOAc) (2 g, 2 mmol) or water and allowed to stir for about 16 h. The precipitated orange solid was filtered, sequentially washed with water/ethanol and hexanes, and dried under vacuum and recrystallized from EtOAc/Hexane to give 1.96 g (73.3%) of Compound 3.

Provenance & Evidence