The glassware used is dried under vacuum and then, once the assembly has been carried out, argon gas is circulated in the latter. The aim of these two operations is to dry as much as possible the medium because thionyle chloride SOCl 2 reacts violently with water. Thionyl chloride is added dropwise to avoid parasitic reactions and to let it react with the bicyclic starting reagent molecule. For this step, two wash bottles are connected to the CaCl 2 guard in order to retrieve and neutralize the toxic gas HCl that is formed during the reaction. The first wash bottle contains water, serves as an intermediary between the assembly and the second bottle to avoid the return of sodium hydroxide NaOH. Thus, the second bottle containing the sodium hydroxide will receive the sulfur dioxide SOCl 2 gas released during the reaction process. The termination of gas bubbles indicates in those bottles the end of the reaction. Afterwards, Dimethyl formamide DMF is added to ensure that the reaction is complete. The remaining traces of this sulfur-containing reagent are removed by codistillation with toluene. This first part was redone under the same conditions due to the fact that our product was deteriorated during the distillation. In fact, we overheated the distillation medium which has led to a brownish, burned product either polymerised or degraded. The product obtained with the second attempt was directly dissolved in 1,4-dioxane and reacted with a solution of concentrated ammonia NH 3 to form the imine near 0 • C for about 18 h, then the medium was at reflux for 4 hours. The reaction mixture was filtered and washed with water to neutralise the pH. Drying under vacuum gave the imine in 113% yield. A yield greater than a 100% shows that the obtained crude contains impurities. This result isn't suprising since the distillation was not conducted on the second attempt of the synthesis. We might still have remaining traces of sulfur-containing reagent.