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Synthesis method of N-hydroxynaphthalimide trifluoromethanesulfonate

A technology of hydroxynaphthoimide trifluoromethanesulfonate and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of difficult degradation of organic bases, unfavorable recovery, high boiling point, etc., and achieve easy recovery, high product yield, and improved The effect of reaction rate

Active Publication Date: 2020-12-18
河北凯力昂生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Methanol recrystallization obtains the target product, and the yield is 30%, but the first step uses DMF as a solvent, which has a high boiling point, which is not conducive to recovery. The second step uses acetonitrile as a solvent, which is extremely volatile and has certain toxicity, and the yield is low. Pyridine is the reaction catalyst, and the organic base used in the process is biodegradable

Method used

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  • Synthesis method of N-hydroxynaphthalimide trifluoromethanesulfonate
  • Synthesis method of N-hydroxynaphthalimide trifluoromethanesulfonate
  • Synthesis method of N-hydroxynaphthalimide trifluoromethanesulfonate

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 330 mL of solvent toluene and 100 g of N-hydroxy-1,8-naphthalimide to a 1L four-necked flask equipped with a stirring paddle, a condenser, and a thermometer, start stirring, and cool down to a reaction system temperature of 8°C. Slowly add 79g of trifluoromethanesulfonyl chloride dropwise to the reaction system, and keep the reaction for 6h. Monitor the reaction process. After the reaction is detected by TCL, 134g of NaOH solution with a mass concentration of 14% is added dropwise to the system after the sampling and detection is completed, and it is uniform after stirring for 30min. Under the action of the solvent toluene, the phases are extracted and separated, and after standing and layering, the extracted toluene phase is concentrated under reduced pressure at 55-65°C. The pressure is 0.099MPa-0.1MPa, the temperature is cooled to room temperature, and the wet product obtained by suction filtration is the crude product of N-hydroxynaphthoimide trifluoromethanesul...

Embodiment 2

[0029] Add 330 mL of solvent xylene and 100 g of N-hydroxy-1,8-naphthalimide into a 1L four-necked flask equipped with a stirring paddle, condenser, and thermometer, start stirring, and cool down to a reaction system temperature of 5°C. Slowly add 79g of trifluoromethanesulfonyl chloride dropwise to the reaction system, and keep the reaction for 7h. Monitor the reaction process, and after the sampling and detection is completed, add dropwise Na to the system with a mass concentration of 14%. 2 CO 3 The solution was 177g, and it was homogeneous after stirring for 30 minutes. Under the action of the solvent xylene, the phases are extracted and separated, and after standing and layering, the xylene phase is concentrated under reduced pressure at 65-75°C. MPa-0.1MPa, cool down to room temperature, and get the wet product by suction filtration, which is the crude product of N-hydroxynaphthoimide triflate. The crude product is passed through 4 times the weight of 20% toluene / 80% w...

Embodiment 3

[0031] Add 330mL of solvent benzene and 100g of N-hydroxy-1,8-naphthalimide to a 1L four-necked flask equipped with a stirring paddle, a condenser, and a thermometer, start stirring, and cool down to a reaction system temperature of 10°C. Slowly add 79 g of trifluoromethanesulfonyl chloride dropwise to the reaction system, and keep the reaction for 5 hours. Monitor the reaction process, after sampling and testing, add dropwise 188g of NaOH solution with a mass concentration of 10% to the system, stir for 30min and then make it uniform. Under the action of the solvent benzene, the phases are extracted and separated, and after standing and layering, the benzene phase is concentrated under reduced pressure at 50-60°C. The condition of the reduced-pressure concentration in this example is 55°C, and the pressure of the reduced-pressure concentration is 0.099MPa -0.1MPa, cool down to room temperature, and obtain wet product N-hydroxynaphthoimide trifluoromethanesulfonate crude produ...

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Abstract

The invention relates to a synthesis method of N-hydroxylnaphthalimide trifluoromethanesulfonate, and belongs to the field of organic synthesis. The method comprises the following steps: (1) taking N-hydroxyl-1,8-naphthalimide and trifluoromethanesulfonyl chloride as raw materials, aromatic hydrocarbon as a solvent and an alkaline solution as a catalyst to carry out esterification reaction, and after the reaction is finished, extracting and concentrating to obtain an N-hydroxylnaphthalimide trifluoromethanesulfonate crude product; and (2) recrystallizing the N-hydroxylnaphthalimide trifluoromethanesulfonate crude product obtained in step (1) to obtain N-hydroxylnaphthalimide trifluoromethanesulfonate, wherein a mixed solution of methylbenzene and water is used as a recrystallization solvent in the recrystallization process. The synthesis method is high in efficiency and high in yield, and the prepared N-hydroxylnaphthalimide trifluoromethanesulfonate is high in purity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular, the invention relates to a synthesis method of N-hydroxynaphthoimide trifluoromethanesulfonate. Background technique [0002] N-hydroxynaphthoimide trifluoromethanesulfonate is mainly cationic photoinitiator, non-ionic photoacid generator and other additives. It is a widely used optical material, mainly used in the manufacture of surface modified polymer films , used to prepare positive tone photoresist, obtain patterned film by photolithography, used to synthesize photoresist composition, used to produce composite materials, including substrates and coatings coated on the surface of substrates, etc. . It has great research value and market prospect. [0003] The report about the synthesis of N-hydroxynaphthoimide trifluoromethanesulfonate mainly is divided into following two classes at present, is summarized as follows now: [0004] ①Using N-hydroxy-1,8-naphthalimide and triflu...

Claims

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Application Information

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IPC IPC(8): C07D221/14
CPCC07D221/14
Inventor 张琛孙佳伟李石磊杜照磊
Owner 河北凯力昂生物科技有限公司
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