Phenylacetic Acid → HCID 54319241, compound

Participants

Reaction Steps

A mixture of phenylacetic acid (10 mmol) in SOCl2 (4 ml, apr. 50 mmol) was stirred for 16 h at room temperature, then evaporated and kept at 2 mm Hg for 0.5 h to remove residual SOCl2. A suspension of 4,5-dichloro-2-nitroaniline (1.035 g, 5 mmol) in ethanol-free CHCl3 (10 mL) was added to the residue and the mixture was stirred at 50° C. for 4 h. It was then cooled to room temperature and evaporated. The residue was treated with ether (100 mL). Precipitated crude product was filtered, washed with ether (5×20 mL) and dried on air to give the title compound. Yield 90%; mp 116°-118° C. (from EtOH); (Lit., 118° C., Ahmad, Yu., et al., Tetrahedron 21:861 (1965)).

Provenance & Evidence