Ethanol → Ethyl 3-(ethylamino)-4-phenoxy-5-sulfamoylbenzoate

Participants

Reaction Steps

A mixture of 3-amino-4-phenoxy-5-sulphamyl-benzoic acid (3.08 g), ethyl iodide (20 ml), and ethanol (20 ml) was refluxed for 6 days. After cooling, the reaction mixture was evaporated to dryness, and the residue was washed with a little ethanol followed by diethyl ether. The ethyl 3-ethylamino-4-phenoxy-5-sulphamyl-benzoate obtained was dissolved in 1N sodium hydroxide (35 ml) and heated on a steam bath for 30 minutes. After cooling, the reaction mixture was adjusted to pH 2.5 by addition of 4N hydrochloric acid, and the precipitated 3-ethylamino-4-phenoxy-5-sulphamyl-benzoic acid was isolated by filtration. After recrystallization from ethanol and drying in vacuo at 115° C, the compound was obtained with a melting point of 236°-237° C.

Provenance & Evidence