Method for synthesizing benzothiadiazine dioxide acetanilide derivative by one-pot method

A technology of benzothiadiazine and dioxide, which is applied in the field of one-pot synthesis of benzothiadiazine dioxide acetanilide derivatives, can solve the problem of increasing the complexity of process operations, waste water and liquid discharge, and increasing labor costs. Cost and environmental protection costs, synthetic methods need to be improved, etc., to achieve the effect of reducing use and manual operation costs, optimizing the sequence of addition, and reducing manual operations

Pending Publication Date: 2021-09-03
CHINA LUCKY FILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the patent CN200310110359.6, Fuji Corporation of Japan introduced the application of such substances as yellow couplers in detail, and briefly described the synthesis route, which involved benzothiadiazine dioxide ethyl acetate Compound synthesis route of benzothiadiazine dioxide acetanilide compound, each step of reaction in this route needs aftertreatment and discharge operation, part of the reaction also needs reduced pressure conditions and there is also a large difference in the order of addition of subsequent reactions Inconvenient, virtually increases the complexity of process operations and the discharge of waste water and liquid, increases labor costs and environmental protection costs
[0004] Therefore, the synthetic method of existing benzothiadiazine dioxide acetanilide derivatives needs to be improved

Method used

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  • Method for synthesizing benzothiadiazine dioxide acetanilide derivative by one-pot method
  • Method for synthesizing benzothiadiazine dioxide acetanilide derivative by one-pot method
  • Method for synthesizing benzothiadiazine dioxide acetanilide derivative by one-pot method

Examples

Experimental program
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Effect test

Embodiment 1

[0051] To a 500mL three-necked flask equipped with a water separator, add 14.67g of 3-tert-butyl-6-[(2-ethylhexyl)thio]aniline, [2-(3-butoxypropyl)-1,1 -dioxide-2H-1,2,4-benzothiadiazin-3-yl]ethyl acetate 19.10g, aluminum isopropoxide 4.08g, anhydrous aluminum trichloride 0.67g and xylene 30mL, 150 After reacting at ℃ for 2 hours, the temperature was raised to 160℃. After reacting for 5 hours, 100mL of toluene was added. At 5℃, 7.15g of 1,3-dibromo-5,5-dimethylhydantoin was added in batches. After reacting for 1.5h, 5, 5-Dimethyloxazolidine-2,4-dione 16.45g, K 2 CO 3 6.9g, reacted at 60°C for 2h, added toluene and water to extract and separate the liquid after the reaction, washed the organic phase once with dilute acid, washed with water until neutral, concentrated under reduced pressure and added methanol to freeze to precipitate 28.61g of solid. The NMR characterization of the final compound is shown in image 3 shown.

Embodiment 2

[0053] To a 500mL three-necked flask equipped with a water separator, add 16.87g of 3-tert-butyl-6-[(2-ethylhexyl)thio]aniline, [2-(3-butoxypropyl)-1,1 -dioxide-2H-1,2,4-benzothiadiazin-3-yl]ethyl acetate 19.10g, aluminum isopropoxide 4.08g, titanium chloride 0.95g and xylene 30mL, 155°C reaction 2 After 1 hour, the temperature was raised to 165°C. After 5 hours of reaction, 100 mL of toluene was added. At 15°C, 8.58 g of 1,3-dibromo-5,5-dimethylhydantoin was added in batches. After 1.5 hours of reaction, 5,5-Dimethylhydantoin was added. Methyloxazolidine-2,4-dione 8.38g, Na 2 CO 3 8.96g, react at 60°C for 2h, add toluene and water to extract and separate the liquid after the reaction, wash the organic phase once with dilute acid, wash with water until neutral, concentrate under reduced pressure and add ethanol to freeze to precipitate 29.67g of solid. The NMR characterization of the final compound is shown in image 3 shown.

Embodiment 3

[0055] To a 500mL three-necked flask equipped with a water separator, add 16.14g of 3-tert-butyl-6-[(2-ethylhexyl)thio]aniline, [2-(3-butoxypropyl)-1,1 -dioxide-2H-1,2,4-benzothiadiazin-3-yl]ethyl acetate 19.10g, aluminum isopropoxide 4.08g and xylene 30mL, react at 150°C for 2 hours and then heat up to 165°C After 5 hours of reaction, 100 mL of toluene was added, 7.86 g of 1,3-dibromo-5,5-dimethylhydantoin was added in batches at 25°C, and 5,5-dimethyloxazolidine- 2,4-diketone 7.74g, NaHCO 3 6.05g, reacted at 60°C for 2h, added toluene and water after the reaction, extracted and separated the liquid, washed the organic phase once with dilute acid, washed with water until neutral, concentrated under reduced pressure and added acetonitrile to freeze to precipitate 28.92g of solid. The NMR characterization of the final compound is shown in image 3 shown.

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Abstract

The invention discloses a method for synthesizing a benzothiadiazine dioxide acetanilide derivative by a one-pot method, which comprises the steps of (1) mixing [2-(3-butoxypropyl)-1, 1-dioxide-2H-1, 2, 4-benzothiadiazine-3-yl] ethyl acetate, 3-tert-butyl-6-[(2-ethylhexyl) sulfenyl] aniline and a catalyst, and carrying out amine ester exchange reaction; (2) mixing the amine ester exchange product obtained in the step (1) with 1, 3-dibromo-5, 5-dimethyl hydantoin, and carrying out an alpha-position bromination reaction of carbonyl; and (3) mixing the brominated product obtained in the step (2) with 5, 5-dimethyl oxazolidine-2, 4-diketone and alkali, and carrying out nucleophilic substitution reaction. The synthesis method has the advantages of low equipment requirement, simple operation process, small organic solvent dosage and low wastewater and waste liquid discharge, and is very suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical intermediate synthesis, in particular to a method for synthesizing benzothiadiazine dioxide acetanilide derivatives in one pot. Background technique [0002] Benzothiadiazines and their derivatives have shown excellent performance in medicine. It has a wide range of biological and pharmacological activities. Among its many derivatives, benzothiadiazine dioxide acetanilide derivatives are also widely used in the photosensitive industry. Due to its excellent moisture and heat resistance stability, high extinction coefficient (can reduce the amount of coupler and silver, effectively reduce coating thickness) and perfect absorption curve (less harmful absorption), benzothiadiazine dioxide Acetanilide compounds are often used as couplers for color photosensitive materials, and have achieved relatively ideal application effects. [0003] At present, there are few reports on the synthesis of benzothia...

Claims

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Application Information

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IPC IPC(8): C07D417/06
CPCC07D417/06
Inventor 豆静杰康长瑞许士鲁
Owner CHINA LUCKY FILM CORP
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