Preparation of Silica‐bonded Propyl‐diethylene‐triamine‐N‐sulfamic Acid as a Recyclable Catalyst for Chemoselective Synthesis of 1,1‐Diacetates

Abstract

A simple and efficient procedure for the preparation of silica-bonded propyl-diethylene-triamine-N-sulfamic acid (SPDTSA) by reaction of 3-diethylenetriamine-propylsilica (DTPS) and chlorosulfonic acid in chloroform is described. Silica-bonded propyl-diethylene-triamine-N-sulfamic acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature. Catalyst could be recycled for several times without any additional treatment.

Sulfamic Acid and Its N- and O-Substituted Derivatives

“…Silica-bonded propyl-diethylene-triamine- N -sulfamic acid has been prepared from 68 and used for synthesis of 1,1-diacetates by reaction of aromatic aldehydes and acetic anhydride under solvent-free conditions . The catalyst was made from 68 , 3-diethylenetriamine-propylsilica, and chlorosulfonic acid in CHCl 3 .…”

Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles

“…To a magnetically stirred mixture of DTPS (5 g) in CHCl 3 (20 ml) at 0 °C, chlorosulfonic acid (2.00 g, 18 mmol) was added dropwise over 2 h. After the addition was complete, the mixture was stirred for 3 h until all HCl was removed from the reaction vessel. The mixture was filtered, washed with methanol (30 ml), and then dried at room temperature to give SBPDSA as a white powder (5.39 g) [30].…”

Recent Advances in the Synthesis of Biscoumarin Derivatives

“…After investigation of different amounts of the catalyst, solvents, and temperatures, the optimized reaction condition was obtained ( Table 1, entry 26). 41 Silica-bonded n-propyldiethylenetriamine sulfamic acid (SBPDSA) as a solid acid was prepared [63][64][65][66] and its catalytic activity was studied in the synthesis of biscoumarins, which were obtained under optimized condition of the reaction (as 0.06 g of catalyst in water under reflux condition) in high yields. Moreover, SBPDSA showed good activity after five runs, showing recyclability ( Figure 5) (Table 1, entry 27).…”