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Method for synthesizing 2-ethoxycarbonylaminosulfonyl-N,N-dimethyl nicotinamide

A technology of ethoxycarbonylsulfamoyl and dimethylnicotinamide, which is applied in the field of pesticides, can solve the problems of difficult solvent recovery and use, large environmental pollution, and waste of energy, and achieve simple and thorough solvent separation, significant economic benefits, Energy Saving Effect

Active Publication Date: 2012-03-21
ANHUI FENGLE AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because this reaction needs to be carried out at freezing low temperature, so energy will be wasted; and the tail gas produced in the reaction process is carbon dioxide gas, and produces a large amount of saline wastewater, which pollutes the environment greatly, and the subsequent treatment is more troublesome, but according to the prior art It is impossible to completely treat the waste water up to the standard
In addition, because acetonitrile is a polar solvent, it is difficult to separate from water, so it is difficult to recycle and use the solvent, so the production scale is limited to a large extent.
[0006] Another synthetic method is to use acetone as a solvent, potassium carbonate as an acid-binding agent, and react 2-aminosulfonamide-N, N-dimethylnicotinamide with ethyl chloroformate to prepare 2-ethoxycarbonylsulfamate Acyl-N, N-dimethylnicotinamide, although the solvents are different, the use of potassium carbonate has caused a certain degree of pollution to the environment and has not yet been resolved
[0007] It is also reported that toluene is used as a solvent, and the content and yield of 2-ethoxycarbonylaminosulfonyl-N, N-dimethylnicotinamide are low, and toluene is serious to environmental pollution

Method used

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  • Method for synthesizing 2-ethoxycarbonylaminosulfonyl-N,N-dimethyl nicotinamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a 500ml four-neck flask equipped with a thermometer, a stirrer, a dropping funnel, and a condenser tube, add 0.1mol of 2-aminosulfonamide-N,N-dimethylnicotinamide, 60mL of acetone and 40ml of water, and put the Adjust the temperature to about 10°C, and at the same time add 0.16mol ethyl chloroformate and liquid caustic soda dropwise to the reactant, measure the pH value every 10 minutes during the dripping of liquid caustic soda to ensure that the pH value is between 7.5-8.5, such as pH If it is too high or too low, you can stop the dripping of liquid caustic soda or reduce the rate of addition of ethyl chloroformate. Use a condenser tube to control the temperature at 10-15°C to ensure that the addition of ethyl chloroformate is complete, then continue to keep warm for 2 hours, and take a sample to measure the residue. When the content of 2-aminosulfonamide-N,N-dimethylnicotinamide is less than 0.1%, it means the end of the reaction. Raise the temperature, carry out...

Embodiment 2

[0035] In a 500ml four-neck flask equipped with a thermometer, a stirrer, a dropping funnel and a condenser tube, add 0.1mol of 2-aminosulfonamide-N,N-dimethylnicotinamide, 70mL of the acetone solution recovered in Example 1, 30ml of water, lower the temperature to 10°C, add liquid caustic soda and 0.15mol of ethyl chloroformate to the reactant at the same time, after dripping at 10-15°C, continue to keep warm for 2 hours, take samples and measure the residual 2-aminosulfonamide-N, The content of N-dimethylnicotinamide is less than 0.1%. After the reaction is completed, the temperature is raised and the atmospheric pressure is distilled. After recovering the acetone, water is added to adjust the pH value to acidity, and then filtered, washed with water, and dried to obtain the product. The waste water can be discharged after the factory's biochemical treatment reaches the standard, which is basically non-polluting to the environment. The yield of the product calculated by 2-a...

Embodiment 3

[0038] In a 500ml four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a condenser, add 0.13mol of 2-aminosulfonamide-N,N-dimethylnicotinamide, 70mL of the acetone solution recovered in Example 2, Add 40ml of water, add 20 mL of fresh acetone, lower the temperature to 10°C, add liquid caustic soda and 0.195mol of ethyl chloroformate to the reactant at the same time, after dropping at 10-15°C, continue to keep warm for 2 hours, take samples and measure the residual The content of 2-aminosulfonamide-N,N-dimethylnicotinamide is less than 0.1%. After the reaction is completed, the temperature is raised and the atmospheric pressure is distilled. After recovering the acetone, water is added to adjust the pH value to acidity, and then filtered, washed with water, and dried to obtain the product. The waste water can be discharged after the factory's biochemical treatment reaches the standard, which is basically non-polluting to the environment. The yield of...

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Abstract

The invention relates to a novel method for synthesizing 2-ethoxycarbonylaminosulfonyl-N, N-dimethyl nicotinamide. 2-ethoxycarbonylaminosulfonyl-N,N-dimethyl nicotinamide is prepared by the following steps of taking liquid alkali as an acid binding agent; performing reaction of 2-aminosulfamide-N,N-dimethyl nicotinamide and ethyl chloroformate; adding 2-aminosulfamide-N,N-dimethyl nicotinamide into an acetone aqueous solution, adding ethyl chloroformate and liquid alkali into acetone aqueous solution while stirring; preserving heat till the completion of the reaction, distilling and recyclingacetone; filtering; separating; and drying to obtain the finished product. The product prepared by the method saves energy and reduces consumption and achieves the environmental safety; no pollutantssuch as carbon dioxide and salt-containing waste water are generated; and the yield and the content of the 2-ethoxycarbonylaminosulfonyl-N,N-dimethyl nicotinamide is high.

Description

[0001] technical field [0002] The invention belongs to the field of pesticides, and in particular relates to a synthesis method of an intermediate 2-ethoxycarbonylaminosulfonyl-N,N-dimethylnicotinamide for preparing nicosulfuron. [0003] Background technique [0004] Nicosulfuron is a sulfonylurea herbicide for cornfields. Due to its high selectivity, unique mechanism of action, and high safety, it has been widely used as a herbicide in cornfields. Its cost price sells well in the market. Many domestic pesticide manufacturers are producing this product. The synthetic route of nicosulfuron generally uses 2-chloronicotinic acid as the starting material, and the final product is synthesized through steps such as acyl chloride, amination, esterification, and condensation. The steps are many , The process is complex. [0005] Therefore, most manufacturers directly purchase intermediates to synthesize nicosulfuron, among which 2-ethoxycarbonylaminosulfonyl-N, N-dimethylnicot...

Claims

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Application Information

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IPC IPC(8): C07D213/82
Inventor 徐志广赵国平王多斌陈克付林昌志温冬江川安刘堂张海松刘晓晨黄亮施亦敏
Owner ANHUI FENGLE AGROCHEM
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