Separation of enantiomers of a thiazolbenzenesulfonamide compound was performed on a Chiralpak AD column using subcritical fluid chromatography. Effects of alcohol modifier and temperature on the separations were studied. The results revealed that while the main adsorbing interactions were between the hydroxyl group of the analyte and the carbamate group of the stationary phase, chiral discrimination was achieved through an inclusion mechanism within the chiral cavity created along the amylose chains. Analogs and synthetic precursors of the thiazolbenzenesulfonamide studied were also investigated so as to understand the effect of functional groups and configuration of the analyte molecule upon chiral recognition.