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A kind of synthetic method of n-hydroxynaphthoimide mesylate

A technology of hydroxynaphthoimide mesylate and synthesis method, which is applied in the direction of organic chemistry, etc., can solve the problems of difficult product purification, low flash point of dichloromethane, high risk of distillation, etc., and achieve short reaction time , Improve product conversion rate and high reactivity

Active Publication Date: 2022-04-08
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

The ethylene glycol dimethyl ether used in the reaction has a high boiling point, and it is difficult to purify the product in the later stage, and the reaction yield is low. Due to the low flash point of dichloromethane, the distillation risk is high, and because of its low boiling point, the distillation recovery rate is low

Method used

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  • A kind of synthetic method of n-hydroxynaphthoimide mesylate
  • A kind of synthetic method of n-hydroxynaphthoimide mesylate
  • A kind of synthetic method of n-hydroxynaphthoimide mesylate

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add the reaction solvent 118mL toluene and 23.6g N-hydroxy-1,8-naphthalimide to a 500mL four-necked bottle in turn, start stirring, cool down to the temperature of the reaction system at 8°C, and slowly add 12.7g of methyl Sulfonyl chloride, reacted for 7h, after the sampling test was qualified, slowly added 58.76g of sodium carbonate aqueous solution with a mass fraction of 10% to the system, stirred for 30min, uniformed, left to stand and layered, and the oil phase extracted by the reaction solvent toluene, that is, the toluene phase, was at 0.09 Concentrate under the pressure of MPa-0.9MPa, control the concentration temperature to be 55°C-65°C, the concentration temperature in this embodiment is 60°C, and obtain the wet product by suction filtration, which is the crude product of N-hydroxynaphthoimide mesylate. The crude product of N-hydroxynaphthoimide mesylate is completely dissolved in 2 times its volume of recrystallization solvent, and the solid obtained by recry...

Embodiment 2

[0029] Add 142mL of reaction solvent 142mL of benzene and 23.6g of N-hydroxy-1,8-naphthalimide to a 500mL four-necked flask in sequence, start stirring, cool down to the temperature of the reaction system at 5°C, and slowly add 13.3g of methyl Sulfonyl chloride, reacted for 8 hours, after the sampling test was qualified, slowly added 41g of sodium carbonate aqueous solution with a mass fraction of 15% to the system, stirred for 30 minutes, uniformed, allowed to stand for stratification, and the oil phase extracted by the reaction solvent toluene, that is, the benzene phase, was at 0.09MPa Concentrate under the pressure of -0.9MPa, control the concentration temperature at 60°C-70°C, the concentration temperature in this example is 65°C, and obtain the wet product by suction filtration, that is, the crude product of N-hydroxynaphthoimide mesylate. The product is completely dissolved in the solid obtained by recrystallization in 3 times the volume of the crude product of N-hydroxy...

Embodiment 3

[0031] Add 165mL of xylene and 23.6g of N-hydroxy-1,8-naphthalimide to a 500mL four-neck flask in sequence, start stirring, cool down to the temperature of the reaction system at 10°C, and slowly add 13.95g of methylsulfonate to the reaction system dropwise Acyl chloride, reacted for 6h, after the sampling test was qualified, slowly add 32.27g of sodium carbonate aqueous solution with a mass fraction of 20% to the system, stir evenly after 30min, leave to stand for stratification, and the oil phase extracted by the reaction solvent toluene, that is, the xylene phase, is at 0.09 Concentrate under the pressure of MPa-0.9MPa, control the concentration temperature to be 65°C-75°C, the concentration temperature in this embodiment is 70°C, and obtain the wet product by suction filtration, which is the crude product of N-hydroxynaphthoimide mesylate. The product is completely dissolved in the recrystallization solvent obtained by recrystallization of 4 times the volume of the crude pr...

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Abstract

The present invention relates to a synthetic method of N-hydroxynaphthalimide mesylate, which belongs to the field of organic synthesis, and comprises the following steps: (1) taking N ‑Hydroxy‑1,8‑naphthalene dimethylimide and methanesulfonyl chloride are used as raw materials, aromatic hydrocarbons are used as reaction solvents, and alkali solution is used as catalyst to carry out esterification reaction. After the reaction is completed, extract and concentrate to obtain N‑hydroxynaphthalene imide mesylate crude product; (2) the crude product of N-hydroxynaphthoimide mesylate obtained in step (1) is recrystallized to obtain N-hydroxynaphthoimide methanesulfonic acid. During the crystallization process, the mixed solution of toluene and water was used as the recrystallization solvent. The synthesis method is simple to operate and easy to purify, and the prepared N-hydroxynaphthoimide mesylate has high 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 mesylate. Background technique [0002] N-Hydroxynaphthoimide mesylate is mainly a widely used optical material and chemical raw material intermediate, mainly used in the manufacture of surface modified polymer films, the preparation of positive tone photoresist, and the pattern obtained by photolithography Thin films, used to synthesize photoresist compositions, produce composite materials, including substrates and coatings applied on the surface of substrates, etc. It has great research value and market prospect. [0003] What US.6965040 used in the synthetic report about N-hydroxynaphthalimide mesylate at present is to be raw material with methanesulfonic acid and N-hydroxyl-1,8-naphthalimide sodium salt, with ethylene disulfide Alcohol dimethyl ether is used as a solvent, and the reaction is carried out at -...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14
CPCC07D221/14
Inventor 李石磊张琛孙佳伟杜照磊
Owner 河北凯力昂生物科技有限公司