Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors

Abstract

Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.

Simple and Versatile Laboratory Scale CSTR for Multiphasic Continuous-Flow Chemistry and Long Residence Times

“…However, two key challenges exist for these reactions: (i) suppression of overfunctionalization and (ii) control of phase partitioning, which often leads to low-yielding processes. Maurya and Wille have independently shown the use of continuous plug-flow and microreactor technology to provide high selectivity in making monoprotected diamines. , Throughout the reaction, different species partition into separate solvent phasesmaking mixing crucial to this type of system. Our miniaturized CSTR offers a simple platform to optimize an experimental design (i.e., DOE) for this reaction, allowing for a continuously well-mixed biphase to both minimize difunctionalization and maximize product partitioning.…”

One‐Step Synthesis of Dicarboxamides through Pd‐Catalysed Aminocarbonylation with Diamines as N‐Nucleophiles

“…[35] Because anhydrous conditions are used in our case, the formation of triphenylphosphine oxide, indicated by GC-MS analysis (m/z [M] + = 277), suggests that triphenylphosphine is probably involved in palladium reduction. The structures of 4a-f, [36][37][38][39] 5b and 6b were established by NMR spectroscopy and further confirmed by high-resolution mass spectrometry. An attempt to perform the aminocarbonylation of the less reactive bromobenzene under the same conditions, with use of 1,2-diaminoethane as N-nucleophile, was unsuccessful, giving only traces of the desired diamide observed by NMR spectroscopy.…”

“…All compounds were subjected to column chromatography [Silicagel 60 (Merck), 0.063-0.200 mm], or simply recrystallised from solvents (the exact ratios are specified below for each compound). -1,3-diyl)bis(cyclohex-1-enecarboxamide) (2b) N,NЈ-(Butane-1,4-diyl)bis(cyclohex-1-enecarboxamide) N,NЈ-(trans-Cylohexane-1,2-diyl)bis(cyclohex-1-enecarboxamide N,NЈ-(1,4-Phenylene)bis(cyclohex-1-enecarboxamide -1,2-diyl)dibenzamide (4a): [36] [36] 13 N,NЈ-(Propane-1,3-diyl)bis(2-oxo-2-phenylacetamide) -1,4-diyl)dibenzamide (4c): [32,33] N,NЈ-[(1S,2S)-Cyclohexane-1,2-diyl]dibenzamide (4d): [36] N,NЈ-(1,4-Phenylene)dibenzamide (4e): [37,38] Biological Essays: The A549 cells were seeded onto a 96-well culture plate at 1 ϫ 10 4 cells per 0.2 mL of culture medium. After attachment, the cells were incubated with the dicarboxamide compounds at different concentrations (10 -4 to 10 -6 m) for 48 h at 37°C.…”

A practical experiment to teach students continuous flow and physico-chemical methods: acetylation of ethylene diamine in liquid bi-phase

“…, representing a commonly utilised reaction within published chemical research [13][14][15]. The reaction complements existing teachings within the undergraduate curriculum including practical synthetic techniques, S N 2 reactions, protecting group theory and analytical techniques.…”