| 93% |
With sodium hydroxide; at 60℃; |
A solventless grinding method for preparing bis-benzenesulfonimide,First 500 grams (3.185 mol) of benzenesulfonamide and 1009 grams were added(5.733 mol) of pure benzenesulfonyl chloride into a volume of 5Liter stainless steel ball mill for 5 minutes,The benzenesulfonamide and benzenesulfonyl chloride are thoroughly mixed at room temperature;Then in 5 times to the stainless steel ball mill 255 g (6.37 mol)Solid NaOH, the material after each addition of NaOH grinding 3 to 7 minutes,And keep the temperature of the reactants below 60 C for 15 minutes;After the reaction was completed, the reaction was transferred from the ball mill to a 5-liter three-necked flask,The reaction was added 10 times the mass of methylene chloride,Install the condenser, heating, stirring, reflux for 30 minutes, hot filtration,The solid in the funnel was washed three times with hot methylene chloride,The generated NaCl was filtered off and the filtrate was combined; Finally, the filtrate was concentrated under heating at atmospheric pressure,After evaporating 2/3 of the solvent, the remaining material was cooled at room temperature,After crystallization, filtration, to give a precipitate,The precipitate was dried at a temperature of 85 C,That is, bisbenzenesulfonimide product 879 grams, the yield was 93%Purity 98.0%. |
| 89% |
With sodium hydroxide; In isopropyl alcohol; at 50 - 55℃; for 2h;pH 8 - 10; |
To a 500 ml flask was added 100 g of isopropanol,50g of benzene sulfonamide dissolved in the preparation of sodium hydroxide,Isopropanol-sodium alcohol solution (14g isopropyl alcohol dissolved in 26g isopropyl alcohol), water bath temperature, while opening the mechanical stirring,When the temperature to 50-55 C, the solid is completely dissolved, began dropping benzenesulfonyl chloride 62g, while dropping sodium hydroxide,Isopropanol-sodium alcohol solution (28g isopropyl alcohol sodium dissolved in 52g isopropyl alcohol), control system pH value of 8 to 10,Control the rate of dropping, dropping finished in 50-55 C for 2h, through the hydroxide anion exchange resin.The reaction solution was cooled to 10 C and centrifuged to obtain BBI sodium salt. The sodium salt is dissolved in hot water,Crystals were precipitated by lowering the temperature by SAPPS cation exchange resin, and the crystals were vacuum dried at 40-50 C,To obtain 84.7 g of solid bis-benzenesulfonimide. As shown in Fig. 7, the results of the HPLC detection showed: benzenesulfonamide: 0.02%;Benzenesulfonyl chloride: 0.02%; NaCl: 0.08%; BBI: 99.96%; Yield: 89%. |
| 21% |
With dmap; triethylamine; In toluene; at 70℃; for 12h; |
General procedure: A mixture of the appropriate arylsulfonyl chloride (11.2 mmol), the corresponding arylsulfonamide (12.3 mmol), DMAP (0.274 g, 2.24 mmol), and Et3N (1.95 mL, 14.0 mmol) in toluene (0.5 M) was kept at 70 C for 12 h (monitored by TLC). The reaction was quenched with aq 2 M HCl (30 mL) to pH 1. The mixture was extracted with EtOAc (3 × 20 mL) and the combined organic layers were dried (anhydrous MgSO4). The solvent was evaporated, and the crude product mixture was purified by recrystallization using hot CHCl3/hexane to afford the desired product. |
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