Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imine

Abstract

The invention relates to a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imine, and belongs to the technical field of chemical engineering. The method comprises the following steps: dissolving trifluoromethanesulfonic acid and organic alkali in an organic solvent, and adding HATU for reaction; the reaction temperature is greater than or equal to 15 DEG C, and the organic solvent is not boiled; after the reaction is finished, a reaction solution containing trifluoromethanesulfonic acid active ester is obtained; adding aniline into the reaction liquid, and reacting at 25 + / -5 DEG C for 6-12 hours; and after the reaction is finished, removing the organic solvent to obtain a crude product containing the N-phenyl bis (trifluoromethanesulfonyl) imine, washing, and recrystallizing and purifying by using an alcohol solvent with 1-3 carbon atoms to obtain the N-phenyl bis (trifluoromethanesulfonyl) imine. The N-phenyl bis (trifluoromethanesulfonyl) imine with high purity and high yield can be prepared by the method, the reaction condition is mild, the utilization rate of raw materials is high, and the method is green and environment-friendly.

Description

technical field [0001] The invention relates to a preparation method of N-phenylbis(trifluoromethanesulfonyl)imide, which belongs to the technical field of chemical industry. Background technique [0002] N-Phenylbis(trifluoromethanesulfonyl)imide is an efficient trifluoromethanesulfonylating reagent, which can carry out acylation reaction with aliphatic aldehydes and ketones (enols), phenols, amines and other groups , and is used in the synthesis of the active ingredient abiraterone API of anti-prostate cancer drugs, so N-phenylbis(trifluoromethanesulfonyl)imide is widely used in pesticides, pharmaceutical intermediates and organic materials. [0003] At present, the synthetic route of N-phenylbis(trifluoromethanesulfonyl)imide has the following three schemes: [0004] Scheme 1: Chinese patent application CN111269152A discloses the use of trifluoromethanesulfonyl fluoride and aniline as reaction raw materials, organic base as acid-binding agent, and 4-dimethylaminopyridine...

AI Technical Summary

Problems solved by technology

But there are following problems in this method: (1) the purity of the N-phenylbis(trifluoromethanesulfonyl)imide that (1) this method makes is low

(2) In the preparation process, the solvent needs to be replaced, and the operation is complicated

(3) The trifluoromethanesulfonyl fluoride product is usually mixed with hydrogen fluoride gas. In the reaction of preparing N-phenylbis(trifluoromethanesulfonyl)imide, hydrogen fluoride will consume aniline and organic base, and hydrogen fluoride will also be mixed with The DMAP reaction deactivates DMAP and affects the reaction yield; and hydrogen fluoride is highly corrosive, it is also necessary to design an anti-leakage device during the reaction to avoid leakage of hydrogen fluoride

But this method has the following problems: (1) the group utilization rate of trifluoromethanesulfonic anhydride in this reaction is not high, causes the waste of raw material; (2) trifluoromethanesulfonic anhydride is expensive, and 1.0eq aniline is at least among the reaction Consume 2.0eq trifluoromethanesulfonic anhydride; (3) reaction system needs dripping trifluoromethanesulfonic anhydride under stirring at low temperature because the exothermic intensity of early stage; (4) this reaction can generate a large amount of trifluoromethanesulfonate and many Organic waste liquid, resulting in low purity of the product, and the reaction conditions are harsh, must meet the protection of inert gas, low temperature control and slow dropwise addition to ensure the reaction yield

In this method, since the ionic liquid is not sold in the market, and the preparation process is relatively complicated, the preparation cost is high, and it is difficult to produce industrially.