Triethylamine → HCID 13746018, compound

Participants

Reaction Steps

A slurry of p-nitrocinnamic acid (1.9 g, 9.8 mmole, Aldrich) and 22 mL dry benzene was stirred under N2 at 0° C. as oxalyl chloride (2.2 mL, 25.2 mmole) was added dropwise. The reaction mixture was stirred at reflux for 11/4 hr, was cooled to room temperature and evaporated. Benzene was added and evaporated several times. The acid chloride was dissolved in ca 15 mL CH2Cl2, and was added dropwise to a 0° C. solution of the compound of example 5 (free base, 1.9 g, 8.2 mmole) in 25 mL CH2Cl2, and triethylamine (1.6 mL, 11.5 mmole). The reaction mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the layers were separated. The aqueous layer was extracted twice with CH2Cl2. The combined organic layers were washed with 1N HCl, saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO 4), filtered, and evaporated (in-vacuo) to yield a tan solid which was triturated with Et2O to yield 2.68 g tan solid (80%); mp 231°-4°.

Provenance & Evidence