2-(2,4-Dichlorophenoxy)acetic acid and its derivatives are promising anti-inflammatory agents capable of selectively inhibiting the COX-2 enzyme. In this paper, we report on the synthesis of a series of new derivatives of 2-(2,4-dichlorophenoxy)acetic acid - 2-(2,4-dichlorophenoxy)-N-(2,2,2-trichloro-1-(3-arylthioureido)ethyl)acetamides. The method for the synthesis of these compounds is based on the addition of aromatic amines to 2-(2,4-dichlorophenoxy)-N-(2,2,2-trichloro-1-isothiocyanatoethyl)acetamide. Target products were obtained in 58-72% yield. The structure of the obtained compounds was reliably proven by ¹Н and ¹³С NMR spectroscopy data. In order to establish the prospects of the synthesized compounds as potential anti-inflammatory agents, we carried out molecular docking studies with COX-2. Molecular docking was carried out using the AutoDock Vina program based on the PyRx 0.8 platform. The preparation of the enzyme structure (PDB ID: 4M11, Mus musculus) and structures of potential inhibitors was carried out using the Chimera 1.14 and ArgusLab 4.0.1 programs, respectively. The conformation corresponding to the lowest energy was chosen as the most likely binding position. According to the results of molecular docking, the structures of the synthesized compounds effectively interact with the active site of COX-2 and surpass 2-(2,4-dichlorophenoxy)acetic acid in terms of the strength of the complex formed with this enzyme.