A series of benzothiazole-based Schiff base esters 6-methyl-2-(4 alkanoyloxybenzylideneamino)benzothiazole (BTHCn), where n denotes the number of carbon atoms in the alkanoyloxy chain (n = 12, 14, 16 and 18), were successfully synthesized. The characteristics and mesomorphic properties of the liquid crystals were also determined. The synthesis was first carried out through Schiff base condensation to produce Schiff base linkage as the main feature in the structure. Schiff base intermediate synthesized, BABT reacted with fatty acid to produce an ester liquid crystal (BTHCn). The structures of the compounds were investigated through Fourier-Transform Infrared (FTIR) spectroscopy, 1D- and 2D-Nuclear Magnetic Resonance (NMR) spectroscopy, and Ultraviolet-Visible (UV–Vis) spectroscopy. Purity and physical characteristics were examined by determining the melting point and Thin Layer Chromatography (TLC). Thermal and mesomorphic characteristics were analyzed through Differential Scanning Calorimetry (DSC). BTHCn homologues displayed distinctive mesophases, with differences transition temperatures influenced by the alkanoyloxy chain length