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A sulfonic acid inner salt compound of amidine

A technology for sulfonic acid inner salts and compounds is applied in the design and synthesis of organic amidine salts, and achieves the effects of strong practical operability, wide sources and good atom economy.

Active Publication Date: 2017-06-13
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report on the synthesis of internal sulfonic acid compounds of amidines. Considering the outstanding performance of other internal salt structures of amidines in various fields, a new type of internal sulfonic acid salts of amidines has been designed and synthesized in anticipation of its application in practical fields. and development is necessary

Method used

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  • A sulfonic acid inner salt compound of amidine
  • A sulfonic acid inner salt compound of amidine
  • A sulfonic acid inner salt compound of amidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment one: 3,5-dimethyl-2-aminobenzenesulfonyl chloride and N,N Synthesis of sulfonic acid inner salt compound of amidine by reaction of dimethylformamide

[0018] Add 219 mg 3,5-dimethyl-2-aminobenzenesulfonyl chloride (1 mmol) and 88 mg N,N - Dimethylformamide (1.2 mmol), stirred reaction at 25°C for 4 hours. After the reaction, add enough methanol and dichloromethane mixed solution to dissolve the reaction system into a homogeneous phase, add silica gel, remove the organic solvent under reduced pressure, and the residue is subjected to silica gel column chromatography (gradient elution, eluent is methanol / dichloromethane). Chloromethane system, the volume ratio is 1:5-1:30) to obtain 210 mg of white solid with a yield of 82%.

[0019] The structural formula of the obtained product and the main NMR test data are as follows, and it can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis;

[0020]

[0021]...

Embodiment 2

[0022] Embodiment two: 3,5-dimethyl-2-aminobenzenesulfonyl chloride and N,N Synthesis of sulfonic acid inner salt compound of amidine by reaction of dimethylformamide

[0023] Add 219 mg 3,5-dimethyl-2-aminobenzenesulfonyl chloride (1 mmol) and 110 mg N,N - Dimethylformamide (1.5 mmol), stirred reaction at 25°C for 2 hours. After the reaction, enough mixed solution of methanol and dichloromethane was added to dissolve the reaction system into a homogeneous phase, then silica gel was added, the organic solvent was removed under reduced pressure, and the residue was separated by silica gel column chromatography to obtain 233 mg of a white solid with a yield of 91%. . The NMR data of the product are the same as in Example 1.

Embodiment 3

[0024] Embodiment three: 3,5-dimethyl-2-aminobenzenesulfonyl chloride and N,N Synthesis of sulfonic acid inner salt compound of amidine by reaction of dimethylformamide

[0025] Add 219 mg 3,5-dimethyl-2-aminobenzenesulfonyl chloride (1 mmol) and 110 mg N,N - Dimethylformamide (1.5 mmol), stirred reaction at 25°C for 4 hours. After the reaction, enough mixed solution of methanol and dichloromethane was added to dissolve the reaction system into a homogeneous phase, silica gel was added, the organic solvent was removed under reduced pressure, and the residue was separated by silica gel column chromatography to obtain 254 mg of white solid with a yield of 99%. . The NMR data of the product are the same as in Example 1.

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Abstract

The invention discloses a sulfonic acid inner salt compound of amidine, which uses an anthranilyl sulfonyl chloride compound and an amide as reactants, and is stirred and reacted to obtain the product amidine sulfonic acid inner salt. The synthesis method of the amidine sulfonic acid internal salt compound disclosed by the invention is simple in operation, mild in reaction conditions, good in yield, and universal to various amides; no reaction solvent is needed, and the environmental pollution is small; the source of raw materials used is wide and easy to obtain ; The synthesis process is simple and controllable, and the practical operation is strong; the atom economy of the reaction is good, and the only by-product is hydrogen chloride gas, which is easy to absorb or recycle; it is suitable for large, medium and small-scale synthesis, and has the potential for industrial application.

Description

technical field [0001] The invention belongs to the technical field of design and synthesis of organic amidine salts, and in particular relates to a novel amidine sulfonic acid inner salt compound. Background technique [0002] Organic amidine salts are widely used in medicine, pesticides, and chemical synthesis. Therefore, the synthesis methods and application development of various organic amidine salts, including hydrochloride, sulfonate, and carboxylate, have been widely studied. and in-depth research; for example, the dihydroxyethylsulfonate or dimethanesulfonate of Pentamidine is an effective drug for treating protozoan infection and preventing pneumonia; the maleate of Pafuramidine can be used as an experimental treatment for Pneumocystis pneumonia Sexual drugs; the dihydrochloride and dipropionate of Imidocarb are new anti-piriform (scorch) drugs with both preventive and therapeutic effects; the diacetyl glycinate of DiminazeneAceturate is a traditional antiparasitic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/32C07C309/15C07D291/08C07D307/68C07D295/195C07D207/22C07D223/12C07D209/40
Inventor 徐凡方吴伟姚志刚
Owner HUAWEI TEHCHNOLOGIES CO LTD
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