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SELECTBIO Conferences Flow Chemistry India 2018


Synthesis of Amines, Carbamates and Amides by Multi-Step Continuous Flow Synthesis: A Step towards Enabling Sustainable Chemical and Drug Manufacturing in Africa

Cloudius Ray Sagandira, Doctoral Student, Nelson Mandela University

Organic azides are valuable and versatile intermediates in organic synthesis. However, they are potentially highly toxic and explosive which makes their handling difficult. These safety concerns can be mitigated by continuous flow multi-step synthesis where the isolation is not necessary. As part of our ongoing program into local drug manufacture, we were interested in further studying the in situ synthesis of acyl azide chemistry in continuous flow systems with a view to conducting multistep synthesis of amines, carbamates, and amides (Figure 1). We report the continuous flow synthesis of acyl azides in various continuous flow systems and demonstrate that liquid-liquid separation may be incorporated to prepare anhydrous solutions of the acyl azide, which may be subsequently reacted with appropriate nucleophiles to prepare amines, carbamates and amides within a fully integrated multi-step process in high yields (>80%). Interesting effects were also observed when preparing carbamates with long chain alcohols, whereby as the chain length of the alcohol increased the products could be made in high yield even without incorporation of the liquid-liquid separation module. 

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