We report a green, metal-free, and efficient synthetic protocol for the preparation of bis-benzothiazoles via benzotriazole-mediated activation of dicarboxylic acids. This methodology employs N-acylbenzotriazole intermediates, which react with 2-aminothiophenol under mild conditions in acetic acid to afford the target bisbenzothiazoles in excellent yields. The process avoids the use of toxic reagents, metal catalysts, and harsh conditions, offering a sustainable alternative to conventional methods. Density functional theory (DFT) calculations provide mechanistic insights and thermodynamic profiles, highlighting the role of substituent effects and noncovalent interactions in product stability. The protocol demonstrates broad substrate scope, operational simplicity, and high atom economy, making it a valuable contribution to green heterocyclic synthesis.