To develop and optimize this reaction, three model components that can be tracked by NMR were selected: acetophenone 1a, aniline 1b, and azide 1c. Our starting point was to apply conditions that resemble the aforementioned initial studies; thus, alcohols seemed to be an ideal solvent choice. Because conditions that are known to facilitate imine formation between acetophenone and aniline, such as elevated reaction temperatures, were also required, butanol was selected due to its high boiling point. Thus, we placed all three components under reflux in butanol and to our delight 44% of the desired product was obtained (Ta-ble1. entry 2). Based on the hypothesized reaction mechanism, we speculated that molecular sieves (MS) could have a positive effect on the conversion by sequestering water released in the formation of the imine intermediate. However, upon the addition of MS to the reaction mixture the yield decreased (Table1. entry 3). We suspected that the basicity of molecular sieves could have negatively affected the conversion. Thus, we suspended MS at the top of the reaction tube with filter paper (see Figure in SI), which led to a significant increase in reaction yield (Table1. entry 1). We then tested toluene and DMSO as solvents because they are commonly used in imine formation reactions, yet in both cases the yield was slightly diminished (Table1. entry 4, 5). We also tested a solvent-free reaction and maintained decent yields (Table1. entry 6). When lowering the temperature to 100 ºC we observed a significant decrease in product formation, and lowering the temperature further to 80 ºC was associated with negligible product yield (Table1. entry 7, 8). Finally, we tested the progress of reaction over time and found that the reaction exhibits similar conversions from two hours onward (Table1. entry 9).