Optimization of the Synthesis of 1, 3-Dimethyl-4-Nitro-1H-Benzimidazolium Iodide; Under Basic Conditions
Disciplines
Organic Chemistry
Abstract (300 words maximum)
1, 3-Dimethyl-4-nitro-1H-benzimidazolium iodide is an organic salt, useful as a backbone in carbene synthesis. This compound contains a nitro group, which helps distinguish it from standard 1,3-dimethyl-1H-benzimidazolium salts, allowing the synthesis of novel carbene complexes. This comes at the cost of the salt being more sensitive to the base used in its own synthesis. This sensitivity was observed through difficulty obtaining a pure high yield product. To remedy the sensitivity, the conditions of the synthesis were varied until an optimal procedure was determined. This procedure utilized potassium carbonate as the base. This was due to it being strong enough of a base to allow completion of the reaction, but still weak enough to form minimal unwanted byproducts. The procedure utilized trituration as the purification method due to its utility and simplicity, while still resulting in a very high yield. To determine the purity of the product produced using this method, the product was subjected to 1H NMR. In the 1H NMR results, the only observable impurities present were from the solvents utilized for the NMR and during purification. These results indicated an optimized method for synthesizing highly pure, high yield 1, 3-dimethyl-4-nitro-1H-benzimidazolium iodide had been determined.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Daniela Tapu
Poster/Presentation
Optimization of the Synthesis of 1, 3-Dimethyl-4-Nitro-1H-Benzimidazolium Iodide; Under Basic Conditions
1, 3-Dimethyl-4-nitro-1H-benzimidazolium iodide is an organic salt, useful as a backbone in carbene synthesis. This compound contains a nitro group, which helps distinguish it from standard 1,3-dimethyl-1H-benzimidazolium salts, allowing the synthesis of novel carbene complexes. This comes at the cost of the salt being more sensitive to the base used in its own synthesis. This sensitivity was observed through difficulty obtaining a pure high yield product. To remedy the sensitivity, the conditions of the synthesis were varied until an optimal procedure was determined. This procedure utilized potassium carbonate as the base. This was due to it being strong enough of a base to allow completion of the reaction, but still weak enough to form minimal unwanted byproducts. The procedure utilized trituration as the purification method due to its utility and simplicity, while still resulting in a very high yield. To determine the purity of the product produced using this method, the product was subjected to 1H NMR. In the 1H NMR results, the only observable impurities present were from the solvents utilized for the NMR and during purification. These results indicated an optimized method for synthesizing highly pure, high yield 1, 3-dimethyl-4-nitro-1H-benzimidazolium iodide had been determined.