Method for preparing N-phenyl succinimide

Abstract

The invention relates to a method for preparing N-phenyl succinimide. The method comprises the following steps: step 1, adding A mol of succinic anhydride and B mol of aniline to a reactor, heating the reactor to 100 to 140 DEG C, and refluxing for 30 to 60 min with stirring; and step 2, cooling a mixture obtained in step 1 to room temperature, adding C mL of water to the mixture, cooling to 3 to7 DEG C, adding a strong acid with stirring to adjust the pH to 3 to 4, extraction-filtering, washing, drying products at the temperature of 60 to 100 DEG C, and recrystallizing with water. So a white crystal N-phenyl succinimide is obtained with A:B being equal to 1:(1.2-2) and C being equal to 200A. The method with the heating temperature in the range of 100 to 140 DEG C allows the reaction to be mild, byproducts to be less, and the yield to be more than 80%.

Description

【Technical field】 [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing N-phenylsuccinimide. 【Background technique】 [0002] Succinimide, abbreviated as NHS, also known as succinimide, is a product of acylation reaction between succinic anhydride and amine compounds. [0003] The hydrogen atom on the nitrogen atom of succinimide is weakly acidic, K=3×10 -11 (25°C), it can be substituted by alkali metal to form a salt, and the reaction of this salt with halogenated hydrocarbon can produce a series of N-hydroxyl substituted derivatives, which are very important in organic synthesis, for example, β-amino acid and its derivatives can be synthesized. Therefore, succinimide is mostly used as a raw material for organic synthesis, and can be used to synthesize N-bromosuccinimide or N-chlorosuccinimide. It is also commonly used as an important intermediate for the preparation of medicines and pesticides. Analytical reagents or used...

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Problems solved by technology

[0005] Studies into the synthesis of azolopyrrolidinobenzodiazepinones and related compounds. Oxidativecyclisations, oxidative fragmentations and arrrementatives published by Bertha, Ferenc in Journal of Chemical Research (Miniprint), Volume 2003, Number 12, December 2003, pp.757-758(2) In thereactions of azolylmethyl-N-phenyl-lactams and related compounds with cerium(IV)ammonium nitrate, 1-phenyl-5-(2H-pyrazole-3-carbonyl)-pyrrolidin-2-one is provided as raw material , using acetonitrile as a solvent to prepare N-phenylsuccinimide, but it generates two other by-products, and the reaction time is long, the yield is low, and the solvent is toxic and not environmentally friendly

[0006] In the document Platinum Complex Catalyzed Reductive N-Acylation of Nitro Compounds published by Yoshihisa Watanabe on J.Org.Chem1984,49,4451-4455, it is provided to use nitrobenzene and succinic acid as raw materials and use dioxane as solvent to prepare N-Acylation -Phenylsuccinimide, but its yield is low, and dioxane is toxic, which is not conducive to recovery and endangers the environment

[0007] The chemistry of pentavalent organobismuth reagents.Part 7.The possible role of radical mechanisms in the phenylation process for bismuth(V), and relatedlead( IV), lodine(III), and antimony(V)reagents literature, provide with succinamide and tetraphenylbismuth trifluoroacetate as raw material, take benzene as solvent to prepare N-phenylsuccinimide, However, the cost of raw materials is expensive, the reaction time is long, the yield is low, and the solvent is toxic and not environmentally friendly.