An efficient approach for the regioselective synthesis of (5‐amino‐3‐methylsulfanyl‐1H‐1,2,4‐triazol‐1‐yl)(2‐fluorophenyl)methanone, C₁₀H₉FN₄OS, (3), from the N‐acylation of 3‐amino‐5‐methylsulfanyl‐1H‐1,2,4‐triazole, (1), with 2‐fluorobenzoyl chloride has been developed. Heterocyclic amide (3) was used successfully as a strategic intermediate for the preparation of 2‐fluoro‐N‐(3‐methylsulfanyl‐1H‐1,2,4‐triazol‐5‐yl)benzamide, C₁₀H₉FN₄OS, (4), through a microwave‐assisted Fries rearrangement under catalyst‐ and solvent‐free conditions. Theoretical studies of the prototropy process of (1) and the Fries rearrangement of (3) to provide (4), involving the formation of an intimate ion pair as the key step, were carried out by density functional theory (DFT) calculations. The crystallographic analysis of the intermolecular interactions and the energy frameworks based on the effects of the different molecular conformations of (3) and (4) are described.

中文翻译：

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通过微波辅助的Fries重排，无催化剂和无溶剂地合成2-氟-N-（3-甲基硫烷基-1H-1,2,4-三唑-5-基）苯甲酰胺：X射线结构和理论研究。

（5-氨基-3-甲基硫烷基-1 H -1,2,4-三唑-1-基）（2-氟苯基）甲酮，C ₁₀ H ₉ FN ₄ OS的区域选择性合成的有效方法，（3） ，从3-氨基-5-甲基硫烷基-1 H -1,2,4-三唑的N-酰化反应（1）中，开发了2-氟苯甲酰氯。杂环酰胺（3）已成功用作制备2-氟-N-（3-甲基硫烷基-1 H -1,2,4-三唑-5-基）苯甲酰胺，C ₁₀ H ₉ FN ₄的战略中间体OS，（4），通过在无催化剂和无溶剂条件下进行的微波辅助炸薯条重排。通过密度泛函理论（DFT）计算，进行了（1）的质变过程和（3）的Fries重排以提供（4）的理论研究，其中涉及形成紧密的离子对作为关键步骤。描述了基于（3）和（4）的不同分子构象的分子间相互作用和能量构架的晶体学分析。