Efficient Synthesis of Benzoylacetonitrile in a Continuous Flow Reaction System

다국어 초록 (Multilingual Abstract)

Benzoylacetonitrile is a highly reactive material that can be converted into various heterocyclic compounds and is used as a building block in many organic chemical reactions. Many methods have been reported for the synthesis of benzoylacetonitrile. In this study, using C-N bond activation of N, N-dimethylbenzamide in the presence of LiHMDS for the synthesis of benzoylacetonitrile. The disadvantage of this reaction is that it takes long time to obtain a high yield of product. To solve this problem, a continuous flow reaction system was used. A continuous flow reaction system has advantages in heat and material transfer as compared to a batch reactor, and has advantages in that temperature and pressure conditions that are difficult to apply to a general batch reactor can be applied. Also, by applying the reaction to a continuous flow reaction system, the actual process suitability of the reaction can be predicted. As a result, by converting the benzoylacetonitrile synthesis reaction from a batch reactor to a continuous reaction system, the reaction time was reduced and a higher product yield was obtained. In addition, the suitability of the system was confirmed through synthesis using other amides.

국문 초록 (Abstract)

Benzoylacetonitrile은 반응성이 높은 물질로, 다양한 heterocyclic compounds 로 전환될 수 있어, 많은 유기 화학 반응에서 building block으로 이용된다. Benzoylacetonitrile의 합성에는 많은 방법들이 보고되어왔다. 본 연구에서는 새로운 방법인 LiHMDS 존재하의 N,N-dimethylbenzamide의 C-N 결합 활성화를 이용하여, N,N-dimethylbenzamide와 Acetonitrile로 Benzoylacetonitrile 합성을 진행하였다. 이 반응은 높은 수율을 얻기까지 시간이 많이 필요하다는 단점이 있다. 이러한 문제를 해결하기 위해 연속 흐름 반응 시스템을 이용하였다. 연속 흐름 반응 시스템은 회분식 반응기와 비교하여, 열 및 물질 전달에 이점이 있고, 일반적인 회분식 반응기에는 적용하기 힘든 온도와 압력 조건을 적용할 수 있다는 장점이 있다. 또한, 연속 흐름 반응 시스템으로의 적용을 통해, 반응의 실제 공정 적합성을 미리 예상해볼 수 있다. 결과적으로, Benzoylacetonitrile 합성반응을 회분식 반응기에서 연속반응 시스템으로 전환하여, 반응 시간을 줄였고, 생성물의 더 높은 수율을 얻어냈다. 또, 다른 아마이드를 이용한 합성을 통해 시스템의 적합성을 확인하였다.

목차 (Table of Contents)

• 1. Introduction 1
• 2. Experiments 4
• 2.1. Reagent 4
• 2.2. Apparatus 6
• 2.3. Procedure and Analysis 9
• 2.3.1. Synthesis of benzoylacetonitrile in a batch reactor 9
• 2.3.2. Synthesis of benzoylacetonitrile in a continuous flow reaction system 10
• 3. Results and discussion 11
• 3.1. Synthesis of benzoylacetonitrile in a batch reactor 11
• 3.2. Synthesis of benzoylacetonitrile in a continuous flow reaction system 14
• 3.3. Experiment with different amides 25
• 4. Conclusion 28
• 5. Reference 29