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Synthetic method of sulfonic acid inner salt compound of amidine

A sulfonic acid inner salt and synthesis method technology, which is applied in the field of synthesis of sulfonic acid inner salt compounds, achieves the effects of mild reaction conditions, good atom economy, and strong practical operability

Active Publication Date: 2015-09-30
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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  • Synthetic method of sulfonic acid inner salt compound of amidine
  • Synthetic method of sulfonic acid inner salt compound of amidine
  • Synthetic method of sulfonic acid inner salt compound of amidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment one: 3,5-dimethyl-2-aminobenzenesulfonyl chloride and N,N Synthesis of sulfonic acid inner salt compound of amidine by reaction of dimethylformamide

[0021] 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%.

[0022] 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;

[0023]

[0024...

Embodiment 2

[0025] Embodiment two: 3,5-dimethyl-2-aminobenzenesulfonyl chloride and N,N Synthesis of sulfonic acid inner salt compound of amidine by reaction of dimethylformamide

[0026] 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

[0027] Embodiment three: 3,5-dimethyl-2-aminobenzenesulfonyl chloride and N,N Synthesis of sulfonic acid inner salt compound of amidine by reaction of dimethylformamide

[0028] 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 synthetic method of a sulfonic acid inner salt compound of amidine. According to the synthetic method, an o-amino benzene sulfonyl chloride compound and amide are adopted as reactants, and stirring reaction is carried out to compound and obtain the product, namely, sulfonic acid inner salt of amidine. The synthetic method disclosed by the invention is easy to operate, mild in reaction condition, and relatively good in yield, has universality for various amide, needs no reaction solvent, and causes little environmental pollution; the adopted raw materials are wide in resources and easy to get; the synthetic process is simple, controllable, and high in actual operability; the reaction is good in atom economy; the only by-product is hydrogen chloride gas which is easy to absorb or recycle; the synthetic method is suitable for large, medium and small scale synthesis, and has a 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 synthesis method of a novel amidine sulfonic acid inner salt compound. Background technique [0002] Organic amidine salts are widely used in medicine, pesticides, and special additives. Therefore, the synthesis methods and application development of various organic amidine salts including hydrochloride, sulfonate, carboxylate, etc. have been obtained. Extensive and in-depth research; for example, Pentamidine dihydroxyethylsulfonate or dimethanesulfonate is an effective drug for treating protozoan infection and preventing pneumonia; Pafuramidine maleate can be used as a drug for the treatment of Pneumocystis pneumonia Experimental drugs; Dihydrochloride and Dipropionate of Imidocarb are new anti-piriform (scorch worm) drugs with both preventive and therapeutic effects; Diacetylglycinate of Diminazene Aceturate is a traditional a...

Claims

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Application Information

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Patent Type & Authority Applications(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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