Preparation method for arylamine benzamides compounds and N-aryl-arylamine benzamides compounds

Abstract

The invention provides a preparation method for arylamine benzamides compounds and N-aryl-arylamine benzamides compounds and belongs to the technical field of refining. According to the method provided by the invention, carbon nitrogen coupling reaction is performed by using arylboronic acid (or borate) as an aryl reagent under a copper-catalyzed condition, the reaction is performed at 10-35 DEG C and the selective arylation of aminophenamide is realized. Compared with the present Buchwald-Hartwig carbon nitrogen coupling reaction under palladium-catalyzed condition, the carbon nitrogen coupling reaction has the advantages that the catalyst is low in cost and low in toxicity, the raw materials are simple, easily acquired, stable and low-toxicity, the reaction temperature is greatly reduced, inert gas atmosphere protection is not required, the stirring reaction can be directly performed in an opening reaction flask under a room temperature condition, the condition is mild and the operation is easy, aniline locally has high-selective arylation reaction, the reaction yield is high, the product is easily purified and the atom economy is high.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of arylaminobenzamide compounds and N-aryl-arylaminobenzamide compounds. Background technique [0002] Aminobenzoyl compounds are important fine chemical intermediates and are widely used in the dye and pesticide industries. Among them, p-aminobenzamide can be used to manufacture Pigment Red 170; anthranilamide derivatives have certain insecticidal or acaricidal activity. The representative compound chlorantraniliprole developed by DuPont shows good field effect and environmental protection. compatibility. Therefore, it is of great significance and practical application value to study the modification methods of aminobenzamide compounds, but in many reactions, the two amino groups on these compounds cannot be well distinguished, which limits the diversity of derivatives and also causes The product is complex, the yield is low, and the pro...

AI Technical Summary

Problems solved by technology

Therefore, it is of great significance and practical application value to study the modification methods of aminobenzamide compounds, but in many reactions, the two amino groups on these compounds cannot be well distinguished, which limits the diversity of derivatives and also causes Problems such as complex products, low yield, and difficult separation

Specific to the selective arylation transformation of the aniline moiety on the aminobenzamide, the Buchwald-Hartwig (Buchwald-Hartwig) reaction with aryl halides under palladium catalysis is usually used at present, but the reaction uses The relatively expensive palladium metal is used as a catalyst, which requires high temperature, and the reaction needs to be carried out under an inert gas atmosphere, which makes the operation complicated and increases the cost of synthesis

In addition, selective arylation can also occur through copper-catalyzed reaction with diaryl periodides, but periodides require additional steps to prepare, and the reaction also needs to be carried out under an inert atmosphere, which is inconvenient to operate

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