Hydrogen Sulfide → Thiobenzamide, 2-bromo-

Participants

Reaction Steps

Gaseous hydrogen sulfide was bubbled into a stirred solution of 1.82 g (10.0 mmol) of 2-bromobenzonitrile, 13 mL of triethylamine and 10 mL of pyridine. After 4 hours, the reaction mixture was poured into 200 mL of ice-water mixture. The resultant oil slowly crystallized. The precipitate was removed by filtration, washed with water (3×) and dissolved in methylene chloride. The organic layer was separated, dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum to give 1.46 g (6.76 mmol, 68%) of the product. 1H NMR (200 MHz, CDCl3): 7.24 (m, 4H), 7.52 (dt, 1H), 8.59 (dd, 1H).

Provenance & Evidence