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Preparation method of benzothiadiazine-1, 1-dioxide compound

A technology of benzothiadiazine and dioxide, which is applied in the field of synthesis of benzothiadiazine-1,1-dioxide compounds, and can solve problems affecting the application of active raw materials, low-efficiency pollution, cumbersome operations, etc. problems, to achieve the effect of eliminating heavy metal pollution, reducing the use of toxic solvents, and improving product yield

Pending Publication Date: 2021-07-16
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods use poisonous and expensive catalysts and a large amount of organic solvents, the reaction yield is low, the operation is cumbersome, the product purity is poor, resulting in waste of resources and environmental pollution
What's more serious is that due to the use of metal catalysts, even after strict post-treatment, traces of highly toxic heavy metals will still be detected in the product, which greatly affects the application of active pharmaceutical ingredients (API) and biological preparations.
[0004] Due to the many problems and deficiencies in the preparation methods in the current literature and patents, which do not meet the development requirements of green chemistry in today's era, the traditional low-efficiency and polluting production methods of such compounds are changed to develop benzothiadiazine-1 , The green and efficient synthesis method of 1-dioxide compounds has important practical significance

Method used

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  • Preparation method of benzothiadiazine-1, 1-dioxide compound
  • Preparation method of benzothiadiazine-1, 1-dioxide compound
  • Preparation method of benzothiadiazine-1, 1-dioxide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A kind of synthetic method of benzothiadiazine-1,1-dioxide compound, the steps are as follows:

[0022] Add 2-aminobenzenesulfonamide (1.0g, 5.80mmol) and benzaldehyde (0.62g, 5.80mmol) into a 25mL round-bottomed flask, heat up to 60°C, and react for 1 hour with the open door open, and monitor the reaction progress with TLC. After the reaction is complete, it is directly separated and dried to obtain off-white 3-phenyl-1,2,4-benzothiadiazine-1,1-dioxide powder. The yield was 98.2%, and the purity was 99.8%.

[0023]

[0024] The product was tested: m.p.: 129–132°C; 1 H NMR (400MHz, DMSO) δ7.90(s,1H),7.72–7.63(m,2H),7.53(d,J=7.2Hz,1H),7.51–7.43(m,3H),7.42(s, 1H), 7.36–7.28(m, 1H), 6.92(d, J=8.3Hz, 1H), 6.77(t, J=7.5Hz, 1H), 5.79(s, 1H); 13 C NMR (100MHz, DMSO) δ144.40, 137.79, 133.33, 129.63, 129.02, 128.06, 124.24, 122.12, 117.22, 116.88, 68.89.

Embodiment 2

[0026] A kind of synthetic method of benzothiadiazine-1,1-dioxide compound, the steps are as follows:

[0027] Add 2-aminobenzenesulfonamide (1.0g, 5.80mmol) and p-tolualdehyde (0.70g, 5.80mmol) into a 25mL round-bottomed flask, heat up to 60°C, and react for 1 hour with the open door open, and monitor the reaction progress by TLC. After the reaction is complete, directly separate and dry to obtain off-white 3-(4-methylphenyl)-1,2,4-benzothiadiazine-1,1-dioxide powder. The yield was 98.2%, and the purity was 96.2%.

[0028]

[0029] The product was tested: m.p.: 153–154°C; 1 HNMR (400MHz, DMSO) δ7.85 (d, J = 11.8Hz, 1H), 7.53 (t, J = 8.7Hz, 3H), 7.42–7.20 (m, 4H), 6.90 (d, J = 8.3Hz, 1H), 6.76(t, J=7.5Hz, 1H), 5.73(d, J=11.7Hz, 1H), 2.35(s, 3H); 13 C NMR (100MHz, DMSO) δ144.40, 139.00, 134.93, 133.28, 129.47, 127.93, 124.22, 122.05, 117.14, 116.84, 68.67, 21.30.

Embodiment 3

[0031] A kind of synthetic method of benzothiadiazine-1,1-dioxide compound, the steps are as follows:

[0032] Add 2-aminobenzenesulfonamide (1.0g, 5.80mmol) and p-fluorobenzaldehyde (0.72g, 5.80mmol) into a 25mL round-bottomed flask, heat up to 60°C, and react for 1 hour with the open door open, and monitor the reaction progress by TLC. After the reaction is complete, it is separated directly and dried to obtain white 3-(4-fluorophenyl)-1,2,4-benzothiadiazine-1,1-dioxide powder. The yield was 98.3%, and the purity was 99.8%.

[0033]

[0034] The product was tested: m.p.: 176-178°C; 1 H NMR (400MHz, DMSO) δ7.92, J = 11.9Hz, 1H), 7.73 (dd, J = 8.7, 5.5Hz, 2H), 7.58–7.50 (m, 1H), 7.41 (s, 1H), 7.32 (ddd, J=15.1, 7.3, 4.1Hz, 3H), 6.90(d, J=8.0Hz, 1H), 6.82–6.71(m, 1H), 5.81(d, J=11.8Hz, 1H); 13 C NMR (100MHz, DMSO) δ164.31, 161.87, 144.51, 134.39, 134.36, 133.56, 130.58, 130.49, 124.44, 122.33, 117.52, 117.06, 116.11, 115.90, 68.34.

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Abstract

The invention relates to a synthesis method of a benzothiadiazine-1, 1-dioxide compound, and develops a novel solvent-free synthesis method of the benzothiadiazine-1, 1-dioxide compound. No solvent is added in the reaction process, and even part of the product can be obtained through separation without post-treatment. Therefore, the separation and purification process of the product is easy to implement, the reaction time is shortened, the yield of the product is increased, the yield can reach 73%-98%, the purity can reach 96%-99%, the use of toxic solvents is reduced to the greatest extent, and the problems of resource waste, environmental pollution and the like caused by the solvents are fundamentally solved. The method thoroughly eliminates the heavy metal pollution problem in the product from the source, is suitable for preparation of active pharmaceutical ingredients (API), biological agents and the like, and meets the requirements of green chemistry concept.

Description

【Technical field】 [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of benzothiadiazine-1,1-dioxide compounds. 【Background technique】 [0002] Benzothiadiazine-1,1-dioxide compounds are important members of the nitrogen-containing heterocyclic molecular family, and their analogues have been found to be some receptor regulators in vivo. At the same time, it is also a structural scaffold for many important potential drugs. Most of the benzothiadiazine-1,1-dioxide compounds have pharmacological activities, such as antihypertensive, diuretic, edema, and antidepressant. [0003] In the current literature and patents, its preparation method is mainly catalyzed in a solvent system, and the catalysts used include: metal catalysts - iron, copper, palladium, samarium, etc., and oxidants - tert-butanol hydroperoxide and reducing agents - samarium diiodide, etc. These methods use poisonous and expensive catalysts and a lar...

Claims

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Application Information

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IPC IPC(8): C07D285/24C07D417/04C07D285/28
CPCC07D285/24C07D285/28C07D417/04
Inventor 黄爱昊卢俊瑞卢博为谢志强刘金彪崔丽阳王洪博
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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