Hydrochloric Acid → HCID 67321093, compound

Participants

Reaction Steps

A solution of 3-chloro-4-(bromoacetyl)nitrobenzene (546 mg, 1.96 mmol) and thioacetamide (162 mg, 2.15 mmol) in absolute EtOH (8 mL) was stirred at 85° C. for 1 h and cooled to room temperature. Solvent was evaporated in vacuo. A suspension of SnCl2.2H2O (1.46 g, 6.47 mmol) and conc. HCl (2 mL) in absolute EtOH (12 mL) was heated to reflux and the resulting clear solution was added to the residue. The reaction mixture was stirred at reflux for 1 h, cooled to room temperature and poured into a solution of KOH (4.4 g) in water (50 mL) at 0° C. The aqueous layer was extracted with EtOAc (3×) and the combined organics were dried over MgSO4, filtered, and concentrated in vacuo to give 438 mg of the titled product as a dark yellow oil (quant. yield): 1H NMR (400 MHz, DMSO-d6) δ 2.70 (s, 3H), 5.61 (broad s, 2H), 6.59 (dd, 1H), 6.69 (d, 1H), 7.58 (d, 1H), 7.62 (s, 1H); [M+H+]+ m/z 225.

Provenance & Evidence