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1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and preparation method thereof

A technology of thiadiazine hydrochloride and dioxo, which is applied in the field of organic synthesis, can solve problems such as difficulty in obtaining ideal results, difficulty in separation and purification, and low yield, and achieve excellent diuresis, simple process, and excellent antibacterial and anti-inflammatory effects Effect

Active Publication Date: 2015-07-08
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ring closure with aldehyde compounds is also a better method, but when there are substituents at both the 2-position and the 3-position, the yield is not high due to the increased steric hindrance
High-temperature ring closure is easy to produce side reactions, separation and purification are difficult, and it is difficult to obtain ideal results.

Method used

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  • 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and preparation method thereof
  • 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and preparation method thereof
  • 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of 2-nitrobenzenesulfonamide

[0024]

[0025] A mixture of 120.0 g of 2-nitrobenzenesulfonyl chloride (compound 1, 0.78 mol) and ammonium acetate (360.0 g, 4.7 mol) was added to 280 mL of THF, and heated to reflux overnight. The solid was obtained by filtration and vacuum-dried to obtain 86.0 g of yellow solid 2-nitrobenzenesulfonamide (compound 2), with a yield of 80%.

[0026] 1 HNMR (400 MHz, DMSO- d 6 ): δ 8.04 (d, J = 7.6 Hz, 1 H), 7.92 (d, J = 7.6 Hz, 1 H), 7.85-7.80 (m, 4 H). MS (ESI) m / z: 203.0 (M+H + ).

Embodiment 2

[0028] Synthesis of 2-aminobenzenesulfonamide

[0029]

[0030] In the presence of catalyst Pd / C with a mass concentration of 10% (10.0g, 13% / w), a methanol solution of 2-nitrobenzenesulfonamide (compound 2) (80.0g, 0.58mol) was dissolved in 50psi of H 2The hydrogenation reaction occurred overnight at 60°C, the catalyst was removed by filtration, and the filtrate was concentrated to obtain 60 g of off-white solid 2-aminobenzenesulfonamide (compound 3), with a yield of 95%.

[0031] 1 HNMR (400 MHz, DMSO- d 6 ): δ 7.49 (s, 1 H), 7.20-7.17 (m,3 H), 6.75 (d, J = 7.2 Hz, 1 H), 6.57 (t, J = 7.2 Hz, 1 H), 5.80 (s, 2 H). MS (ESI) m / z: 173.0 (M+H + ).

Embodiment 3

[0033] Synthesis of 2-amino-5-bromobenzenesulfonamide

[0034]

[0035] To the suspension of 2-aminobenzenesulfonamide (compound 3) (232.0g, 1.34mol) in acetic acid (2L), add bromine (216.0g, 1.37mol) in acetic acid (1L) dropwise, and stir for another 0.5h. The resulting solution was poured into water to obtain a solid, which was washed with water and dried in vacuo to obtain 300.0 g of white solid 2-amino-5-bromobenzenesulfonamide (compound 4), with a yield of 90%.

[0036] 1 HNMR (400 MHz, DMSO- d 6 ): δ 9.61 (s, 1 H), 8.18 (d, J = 8.0 Hz, 1 H), 7.82 (d, J = 8.0 Hz, 1 H), 7.68 (s, 2 H), 7.53 (t, J = 8.0 Hz, 1 H), 7.25 (t, J = 8.0 Hz, 1 H). MS (ESI) m / z: 251.9 (M+H + ).

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Abstract

The invention discloses a 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and a preparation method thereof, belonging to the technical field of organic synthesis. The technical scheme has the key point as follows: the 1,1-dioxo-4H-benzo[1,2,4]- thiadiazine hydrochloride compound has the structure as shown in the specification, wherein R is H, -CH3 or -C2H5. The invention also discloses the preparation method of the 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound. The preparation method is simple, convenient and easy to operate, relatively high in reaction efficiency and relatively good in repeatability, and raw materials are cheap and available.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and a preparation method thereof. Background technique [0002] Heterocyclic compounds are the largest category of organic compounds, and they are widely distributed in nature. Their chemical structures are also ever-changing, and each has its own unique properties and uses. Nitrogen-containing heterocyclic compounds play an important role in agricultural production such as pesticides and medicines and human health because of their good biological activity. At present, many nitrogen-containing heterocyclic compounds have been developed into new pesticides and pharmaceutical products. 1,2,4-Benzothiadiazine is a class of heterocyclic compounds containing N and S heteroatoms. This heterocyclic compound has a wide range of applications in medicinal chemistry. It is often used as a diuretic to promote...

Claims

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Application Information

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IPC IPC(8): C07D285/24
CPCC07D285/24
Inventor 张丹丹毛龙飞李伟姜玉钦徐桂清董文佩蒋涛申家轩
Owner HENAN NORMAL UNIV
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