Under mechanochemical ball-milling and solvent-free conditions, a series of 2-anilinobenzoxazoles and -thiazoles were synthesized directly from the one-pot reaction of anilines, CS2, and 2-aminophenol and -thiophenol. This protocol exhibits the following advantages: free or cheap use of a cyclodesulfurization reagent, no separation of in situ generated isothiocyanate, short reaction time, and simple work-up procedure.