Having a synthetic and computational strategy in mind, we performed an optimization study using sulfamidate (1a) and benzoic acid (2a) to form the desired product 3a. Reaction conditions from the literature for similar MCRs resulted in a messy TLC and trace product formation as identified using HPLC-MS (entry 1 in Table ). The replacement of a mixture of solvents with only dichloroethane (DCE) and room temperature conditions gave trace amounts of product as detected by HPLC-MS (entry 2). Next, replacing dichloroethane with dichloromethane (DCM) afforded a detectable quantity of desired product 3a (entry 3). While doing a time-point study with a 30 minutes interval, we observed that the desired product was formed within 30 minutes (entry 4). However, TLC analysis shows multiple products, so we decreased the reaction temperature. At 0°C the desired product formed within 5 minutes (entry 5) as determined by a 5 minute time-point study. In all the above attempts, benzoic acid was added slowly. At -10°C, an additional experiment where DCM is added at the end increased the yield significantly (entry 6 vs 7) -suggesting that sulfamidate has high reactivity. a Reactions are at 0.1 mmol scale; b Reaction condition followed as per literature ; c benzoic acid added at the end; d all solid components were taken together and solvent added at the end; e isolated yield; T = Temperature and t = time Next, we applied the optimized reaction condition to the acyclic imine selected using DFT calculations (Figure ) as it was the second most reactive imine. Interestingly, the reaction afforded the desired product with good yield (Scheme 2), but with longer reaction time (10 mins) for the complete conversion as compared to sulfamidate (<5 min). This led us to investigate the mechanism and the energy profile of various plausible intermediates formed in this reaction.