Hydrochloric Acid → HCID 23509862, compound

Participants

Reaction Steps

To a suspension of 3-(4-amino-phenyl)-2-(3-trifluoromethyl-phenyl)-propionic acid (4.0 g, 12.9 mmol) in water (50 ml) and hydrochloric acid (2.8 ml, 32.3 mmol) at 0-5° C. was added sodium nitrite (0.89 g, 12.9 mmol) in water (20 ml). The reaction mixture was warmed to room temperature and poured in a solution of the sodium salt of dithiocarbonic acid O-ethyl ester (4.14 g, 25.8 mmol) in water (20 ml). The reaction mixture was stirred at 60° C. for 2 hours and the precipitate (resin) was solved with ethyl acetate. The organic layer was washed with water, dried, and evaporated in vacuo. The resulting dark brown oil was solved in ethanol (50 ml). At refluxing temperature, sodium hydroxide (3.6 g, 64.5 mmol) was added. After three hours at that temperature, the ethanol was removed, the residue solved in water, and the aqueous layer washed with dichloromethane. To the aqueous layer, potassium hydrogensulfate (10 g) was added. The resulting oil was extracted with dichloromethane, dried, and evaporated in vacuo to give 3.05 g (72%) of the desired product. MS m/z: 327.2 (M+H)+.

Provenance & Evidence