Preparation method of 4-amino-6-(trichloroethenyl)-1, 3-benzene disulfonamide

A technology of trichlorovinyl and benzenedisulfonamide, which is applied in the preparation of 4-amino-6--(trichloroethenyl)-1,3-benzenedisulfonamide and the field of preparation of veterinary drugs, which can solve the problem of low synthesis efficiency , long cycle and other issues to achieve the effect of speeding up the process and productivity

Inactive Publication Date: 2015-04-29
丹阳恒安化学科技研究所有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In each step of the reaction, there are disadvantages such as low synthesis efficiency and long cycle.

Method used

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  • Preparation method of 4-amino-6-(trichloroethenyl)-1, 3-benzene disulfonamide
  • Preparation method of 4-amino-6-(trichloroethenyl)-1, 3-benzene disulfonamide

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Put 30g of m-nitrobenzaldehyde and 15ml of chloroform in 120ml of DMF, cool to -10~-20°C, dissolve 0.9g of cesium carbonate in 20ml of methanol, add dropwise under nitrogen, and keep at -15~-20°C for 2 -3 hours transferred to 200mL toluene and 20mL30% hydrochloric acid solution, the water layer was separated, the organic layer was washed with water, and the water layer was separated; the organic layer was washed with sodium bicarbonate, purified, and then dried to obtain a condensate with a yield of 88 %; After the condensate is chlorinated and eliminated, 50g of the eliminated product is made of methanol-water as a solvent and iron is used as a reducing agent under acidic conditions, and 0.25g of iridium complex [Cp*IrCl 2 ] 2 As a catalyst, a dark red liquid is obtained through reduction reaction at room temperature, with a yield of 92%. Finally, the reduced product is sulfonated with chlorosulfonic acid, ammonified, and purified to obtain 4-amino-6--(trichloroethenyl...

Embodiment 2

[0017] Put 30g of m-nitrobenzaldehyde and 15ml of chloroform in 120ml of DMF, cool to -10~-20°C, dissolve 1.5g of cesium carbonate in 20ml of methanol, add dropwise under nitrogen, and keep at -15~-20°C for 2 -3 hours transferred to 200mL toluene and 20mL30% hydrochloric acid solution, the water layer was separated, the organic layer was washed with water, and the water layer was separated; the organic layer was washed with sodium bicarbonate, purified, and then dried to obtain a condensate with a yield of 90 %; After the condensate is chlorinated and eliminated, 50g of the eliminated product is made of methanol-water as a solvent and iron is used as a reducing agent under acidic conditions, and 0.5g of iridium complex [Cp*IrCl 2 ] 2 As a catalyst, a dark red liquid can be obtained through reduction reaction at room temperature, with a yield of 96%. Finally, the reduced product can be sulfonated with chlorosulfonic acid, ammonified, and purified to obtain 4-amino-6--(trichloro...

Embodiment 3

[0019] Put 30g of m-nitrobenzaldehyde and 15ml of chloroform in 120ml of DMF, cool to -10~-20°C, dissolve 1.2g of cesium carbonate in 20ml of methanol, add dropwise under nitrogen, and keep at -15~-20°C for 2 -3 hours transferred to 200mL toluene and 20mL30% hydrochloric acid solution, the water layer was separated, the organic layer was washed with water, and the water layer was separated; the organic layer was washed with sodium bicarbonate, purified, and then dried to obtain a condensate with a yield of 89% %; After the condensate is chlorinated and eliminated, 50g of the eliminated product is made of methanol-water as a solvent and iron is used as a reducing agent under acidic conditions, and 0.4g of iridium complex [Cp*IrCl 2 ] 2 As a catalyst, a deep red liquid can be obtained through reduction reaction at room temperature, with a yield of 90%. Finally, the reduced product can be sulfonated with chlorosulfonic acid, ammonified, and purified to obtain 4-amino-6--(trichlor...

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Abstract

The invention discloses a preparation method of a veterinary drug 4-amino-6-(trichloroethenyl)-1, 3-benzene disulfonamide. The preparation method comprises the following steps: using m-nitrobenzaldehyde as a raw material, and performing condensation reaction, chlorination reaction, elimination reaction reduction reaction, sulfonation reaction and ammoniation reaction to obtain 4-amino-6-(trichloroethenyl)-1, 3-benzene disulfonamide, wherein a catalyst used in the condensation reaction is cesium carbonate; an iridium complex is used as a catalyst in the reduction reaction. The cesium carbonate is used as the catalyst in the condensation reaction and the iridium complex is used as the catalyst in the reduction reaction, so that the whole reaction process is speeded up, and the prepared veterinary drug is good in quality and high in yield.

Description

technical field [0001] The invention relates to a preparation method of veterinary medicine, in particular to a preparation method of 4-amino-6-(trichloroethenyl)-1,3-benzenedisulfonamide, which belongs to the field of medicine preparation. Background technique [0002] 4-Amino-6--(trichloroethenyl)-1,3-benzenedisulfonamide can inhibit the degrading enzyme of glucose, block the main energy source of liver leeches, and play an anti-worm role. Further studies have shown that 4-amino-6--(trichloroethenyl)-1,3-benzenedisulfonamide can competitively inhibit 8-phosphoglycerate kinase and phosphoglycerate mutase, blocking the oxidation of glucose to acetate Salt and propionate. In addition, 4-amino-6--(trichloroethenyl)-1,3-benzenedisulfonamide can also inhibit the level of adenosine triphosphate (ATP) in liver leeches. After subcutaneous injection of 4-amino-6--(trichloroethenyl)-1,3-benzenedisulfonamide, the maximum plasma concentration level was reached 24 hours after admi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/39C07C303/38
Inventor 陈国平夏方方杜成铭陈丽庆王霞张梁吴涛英荆吉仁夏新开王海大
Owner 丹阳恒安化学科技研究所有限公司
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