Triazole Synthesis via One-Pot Merging
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Solution Overview
Problem
Current processes for preparing 1,3-(substituted-diaryl)-1,2,4-triazoles and their intermediates are complex and require multiple steps, making them less commercially viable for producing pesticides.
Innovation Solution
Development of efficient synthetic routes involving reactions of 3-(bromo, chloro, or iodo)-1H-1,2,4-triazole with haloalkoxy-benzene derivatives using metal catalysts and bases in polar solvents, followed by subsequent reactions with boronic acids or trifluoroborate salts, to produce compounds like 4-(1-(4-trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl benzoic acid and benzoate, which can be used to form pesticidal molecules.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If conventional processes are used to prepare 1,3-(substituted-diaryl)-1,2,4-triazoles, then the compounds can be produced, but the process requires multiple steps making it complex and less commercially viable
Solution Approach 1:
The patent combines multiple reaction steps into a single one-pot process. Specifically, it merges the formation of the triazole ring, the introduction of the haloalkoxy substituent, and the subsequent coupling reaction with boronic acid or trifluoroborate salt into one continuous sequence, eliminating the need for intermediate isolation and purification steps.
Solution Approach 2:
The patent employs preliminary action by pre-forming the triazole ring with the haloalkoxy substituent already in place before introducing the boronic acid or trifluoroborate salt. This preliminary structuring allows the final coupling reaction to proceed directly without requiring separate preparation steps for the triazole intermediate.
2Productivity
If multi-step processes are used, then intermediate compounds can be isolated and characterized, but the overall synthesis time and cost increase
Solution Approach 1:
The patent maintains continuity of useful action by keeping the reaction mixture active throughout the entire synthesis sequence. The triazole formation, substitution, and coupling reactions proceed in sequence without stopping, with reagents added in a predetermined order to maintain continuous productive transformation of the starting materials into the final product.
Solution Approach 2:
The patent segments the reaction into distinct phases within a single pot, with each phase targeting a specific transformation. The first phase forms the triazole ring, the second phase introduces the haloalkoxy group, and the third phase performs the coupling reaction, allowing each transformation to occur under optimized conditions without requiring physical separation.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
These routes simplify the synthesis of triazole intermediates, reducing the number of process steps and enhancing the commercial viability for producing pesticides by providing more efficient and cost-effective pathways.
Implementation Method 1
reactions of 3-(bromo, chloro, or iodo)-1H-1,2,4-triazole with haloalkoxy-benzene derivatives using metal catalysts and bases in polar solvents
Implementation Method 2
subsequent reactions with boronic acids or trifluoroborate salts, to produce compounds like 4-(1-(4-trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl benzoic acid and benzoate
Data Source
AI summary
The invention in this document is related to the field of preparation of 1,3-(substituted-diaryl)-1,2,4-triazoles and certain intermediates derived therefrom, where said intermediates are useful in the preparation of certain pesticides disclosed in U.S. Pat. No. 8,178,658.