Practical and Scalable Synthesis of 5,6-Dichlorofurazano[3,4-b]pyrazine

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2023-08-17 DOI:10.1021/acs.oprd.3c00196

Zhongyu Sun, Yuji Liu, Wei Huang, Ning Liu, Guangbin Cheng, Chuan Xiao* and Yongxing Tang*,

引用次数: 0

Abstract

4H,8H-Difurazano[3,4-b:3′,4′-e]pyrazine (DFP) is an important heat-resistant explosive intermediate, but its current synthesis process is still not scalable due to the low yields and acidic smokes in an internal chlorination step to give the intermediate DHFP. In this work, a DMA-promoted chlorination method to synthesize 5,6-dichlorofurazano[3,4-b]pyrazine is described to solve the bottleneck of DFP synthesis. The best reaction conditions were confirmed to be DMA, DHFP, and POCl₃ (2:1:40) at 120 °C for 3 h, with an increased yield of 62%. This new method not only increases the yield but also eliminates the acid smokes during postprocessing, and it is likely to find practical applications in the synthesis of DFP and other heat-resistant explosives.

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实用及规模化合成5,6-二氯呋扎诺[3,4-b]吡嗪

4H, 8h -双呋喃氮杂[3,4-b:3 '，4 ' -e]吡嗪(DFP)是一种重要的耐热炸药中间体，但由于产率低，并且在生成中间体DHFP的内部氯化步骤中产生酸烟，目前的合成工艺仍不具有可扩展性。为了解决DFP合成的瓶颈，本文提出了一种dma促进氯化合成5,6-二氯呋扎诺[3,4-b]吡嗪的方法。结果表明，最佳反应条件为DMA、DHFP和POCl3(2:1:40)，反应温度120℃，反应时间3 h，产率提高62%。该方法不仅提高了产率，而且消除了后处理过程中产生的酸烟，有望在DFP等耐热炸药的合成中得到实际应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.