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Method for preparing 4, 4 '-oxydiphthalimide

A bis-phthalimide and phthalimide technology, applied in the field of compound preparation, can solve the problems of many by-products of halogenated products, low yield of target products, and easy reaction, and achieve the goal of preparing The method is simple, the yield is high, and the effect of mild reaction conditions

Active Publication Date: 2020-11-24
南京康德祥医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current main method for the synthesis of 4,4'-oxobisphthalimide is to dehalogenate and condense halogenated phthalic anhydride into ether anhydride in the presence of alkali metal compounds and catalysts, and the by-products of halogenated products are many , the yield of the target product is low
Moreover, the hydrogen atom on the imide group is prone to react, causing the problem of low yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0031] A preparation method of 4,4'-oxobisphthalimide, comprising the following steps:

[0032] (1) Dissolve phthalimide in a solvent, add triisopropylchlorosilane and react at 0~30°C to obtain N-triisopropylsilyl-phthalimide;

[0033] (2) Add N-triisopropylsilyl-phthalimide to the solvent, and react with nitric acid in the presence of a catalyst to obtain 4-nitro-N-triisopropylsilyl- Phthalimide;

[0034] (3) Add 4-nitro-N-triisopropylsilyl-phthalimide to the solvent, add a catalyst, and react to obtain 4,4'-oxobis(N-triisopropyl silyl-phthalimide);

[0035] (4) Add 4,4'-oxobis(N-triisopropylsilyl-phthalimide) to the solvent and deprotect in situ with desiliconization reagent to obtain 4,4'-oxo Substituted bisphthalimide;

[0036] The reaction process is as follows:

[0037] .

Embodiment 1

[0039] A preparation method of 4,4'-oxobisphthalimide, comprising the following steps:

[0040] (1) Dissolve 147.03g (1mol, 1 equiv.) phthalimide in 1000mL DMF, add 212.08 (1.1mol, 1.1 equiv.) triisopropylchlorosilane, stir to dissolve, and place at 0°C Reaction 12h obtains 282.6g N-triisopropylsilyl-phthalimide;

[0041] (2) Add 282g (0.932mol) N-triisopropylsilyl-phthalimide to 500mL DMF, stir to dissolve, add 10g concentrated sulfuric acid, add 70.13g (1.1mol) nitric acid, The reaction was stirred at ℃ for 10 h to obtain 290.31 g of 4-nitro-N-triisopropylsilyl-phthalimide;

[0042] (3) Add 290.31g (0.833mol) of 4-nitro-N-triisopropylsilyl-phthalimide to 500mL of DMF, add 10g of potassium nitrate, and react at 150°C for 12h to obtain 450.36 g 4,4'-oxobis(N-triisopropylsilyl-phthalimide);

[0043] (4) Add 450.36g (0.726mol) 4,4'-oxobis(N-triisopropylsilyl-phthalimide) to 800mL DMF, add 274.87g tetrabutylammonium fluoride The trihydrate was stirred at room temperature for ...

Embodiment 2

[0047] A preparation method of 4,4'-oxobisphthalimide, comprising the following steps:

[0048] (1) Dissolve 147.03g (1mol, 1 equiv.) phthalimide in 1000mL DMF, add 212.08 (1.1mol, 1.1 equiv.) triisopropylchlorosilane, stir to dissolve, and place at 15°C Reaction 12h obtains 290.6g N-triisopropylsilyl-phthalimide;

[0049] (2) Add 290.6g (0.960mol) N-triisopropylsilyl-phthalimide to 500mL DMF, stir to dissolve, add 10g of concentrated sulfuric acid, add 70.13g (1.1mol) of nitric acid, in The reaction was stirred at 70°C for 10 hours to obtain 298.21 g of 4-nitro-N-triisopropylsilyl-phthalimide;

[0050] (3) Add 298.21g (0.856mol) of 4-nitro-N-triisopropylsilyl-phthalimide to 500mL of DMF, add 10g of potassium nitrate, and react at 150°C for 12h to obtain 485.44 g 4,4'-oxobis(N-triisopropylsilyl-phthalimide);

[0051] (4) Add 485.44g (0.782mol) 4,4'-oxobis(N-triisopropylsilyl-phthalimide) to 800mL DMF, add 296g tetrabutylammonium fluoride tri Hydrate, stirred at room temper...

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PUM

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Abstract

The invention discloses a method for preparing 4, 4 '-oxydiphthalimide. The method comprises the following steps: dissolving phthalimide in a solvent, adding triisopropylchlorosilane 0-30 DEG C for reaction to obtain N-triisopropylsilyl-phthalimide; adding N-triisopropylsilyl-phthalimide to a solvent and reacting with nitric acid in the presence of a catalyst to obtain 4-nitro-N-triisopropylsilyl-phthalimide; adding 4-nitro-N-triisopropylsilyl-phthalimide to a solvent, adding a catalyst, and reacting to obtain 4,4'-oxobis(N-triisopropylsilyl-phthalimide); adding 4,4'-oxobis(N-triisopropylsilyl-phthalimide) to a solvent, and deprotecting in situ with a desiliconizing reagent to obtain 4,4'-oxobisphthalimide. 4,4'-oxobisphthalimide is obtained through four-step reaction, and the method is simple, has cheap and readily available raw materials, and is suitable for large-scale production.

Description

technical field [0001] The invention relates to a preparation method of 4,4'-oxobisphthalimide, which belongs to the technical field of compound preparation. Background technique [0002] Phthalimide, commonly known as phthalimide, is an intermediate used in the synthesis of many fine chemicals such as phthalide, phthalonitrile, indigo, fungicide fendan, and insecticide imidophos. In addition, it can also be used to produce high-efficiency ion exchange resins, surfactants, etc., and is widely used in industries such as dyes, pesticides, medicine, and rubber. The current market demand in my country is relatively large. [0003] 4,4'-Oxobisphthalimide is one of the important monomers for synthesizing polyimide and polyetherimide. Because of the ether bond in the molecule, its flexibility is significantly enhanced and the polyimide is improved. The defect of high hardness of imide can be used in many high-tech fields such as aerospace, aviation, space, automobile, microelectron...

Claims

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Application Information

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IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 周柳琴纪安成王锋
Owner 南京康德祥医药科技有限公司