Hydrochloric Acid → HCID 178522849, compound

Participants

Reaction Steps

6-Chloro-N-(4-trifluoromethyl-benzyl)-nicotinamide (Preparation 85, 4.0 g, 13 mmol) was added to a warm solution of thiourea (1.01 g, 13.2 mmol) in EtOH (20 mL, 300 mmol). The mixture was heated 1 h at reflux. LC/MS indicated mostly SM. 1 additional equivalent of thiourea was added, and the reaction mixture was heated at reflux. After 16 h, LC/MS shows conversion to the intermediate along with a small amount of product. The reaction mixture was concentrated in vacuo. To the intermediate 6-carbamimidoylsulfanyl-N-(4-trifluoromethyl-benzyl)-nicotinamide; hydrochloride in water (32 mL, 1800 mmol) was added sodium carbonate (1.07 g, 10.1 mmol). After stirring for 15 minutes, sodium hydroxide (1.61 g, 40.3 mmol) in water (2.0E1 mL, 1100 mmol) was added. The reaction mixture was filtered, and the filtrate was slowly acidified with 6 N HCl. The resulting precipitate was collected by filtration, washed with water, and dried under vacuum to afford the product as a bright yellow solid (3.58 g, 86%).

Provenance & Evidence