Dibutylcarbamoyl chloride

UsesIt is reported that Dibutylcarbamoyl Chloride is used as a reagent for the preparation of 7-azaindole-1,3-dicarboxamide hydroxyethylamine which exhibited potent BACE-1 enzyme inhibition. Also it is used for the preparation of copper salicylaldehyde semicarbazone complex which showed cytotoxicity in human cancer cells.

PreparationIn a 100 mL roundbottomed flask were placed dibutylamine (6.45 g, 0.05 mol), pyridine (4.0 g, 0.05 mol), N-cyclohexyl-N0,N0,N00,N00-tetraethylguanidine (12.7 g, 0.05 mol), and toluene (40 mL). The resulting solution was cooled to 10 °C using an ice/salt bath and carbon dioxide was bubbled into the cooled solution for 30 min. After this period of time, the pre-formed carbamate solution was added in a single portion via a cannula to a cooled ( 10 °C) solution of thionyl chloride (6 g, 0.05 mol) in toluene (40 mL). The reaction mixture was stirred at 10 °C for 45 min. It was then poured into 0.1 m aq. HCl (100 mL), giving rise to two layers. The organic layer was separated, dried over anhydrous Mg2SO4, filtered, and the solvent was removed in vacuo. The residue was distilled in vacuo (1 mmHg) at 95–98 °C to give 7.62 g (79%) of N,N-dibutyl carbamoyl chloride.