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Preparation method of intermediate of iodosulfuron-methyl sodium

The technology of iodosulfuron-methyl sodium salt and intermediate is applied in the field of preparation of iodosulfuron-methyl sodium salt intermediate 6-iodosaccharin, and can solve the problems of not meeting environmental protection requirements, not meeting economic requirements, and high cost of treating wastewater, Achieve the effect of avoiding decomposition and hydrolysis, high product yield and low environmental protection cost

Active Publication Date: 2019-08-23
江苏省农用激素工程技术研究中心有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] (2) This method requires a large amount of organic acid and water as a solvent, resulting in more salty wastewater, and the cost of wastewater treatment is higher, which neither meets environmental requirements nor economic requirements

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0030] The reaction formula of the present embodiment is as follows:

[0031] .

[0032] The concrete method of this embodiment is as follows:

[0033] Add 20g (0.101mol) of 6-aminosaccharin, 17.6g (0.106mol) of potassium iodide, 6.4g (0.107mol) of acetic acid and 100g of toluene into a 500mL reaction bottle, and drop 11.8g (0.101mol) of isoamyl nitrite at about 10°C mol), reacted at 20°C for 2 hours after dropping, then added 20g of water, stirred for 10 minutes, allowed to stand for stratification, added 15g of sodium carbonate aqueous solution with a concentration of 10wt% to the organic layer, stirred for 10 minutes, stood for stratification, The organic layer was precipitated to obtain 28.1 g of 6-iodosaccharin with a content of 96% and a yield of 90.0%.

Embodiment 2）

[0035] The reaction formula of the present embodiment is as follows:

[0036] .

[0037] The concrete method of this embodiment is as follows:

[0038] Add 20g (0.101mol) of 6-aminosaccharin, 17.6g (0.106mol) of potassium iodide, 6.4g (0.107mol) of acetic acid and 100g of toluene into a 500mL reaction bottle, and add 10.4g (0.101mol) of n-butyl nitrite dropwise at about 10°C mol), reacted at 20°C for 2 hours after dropping, then added 20g of water, stirred for 10 minutes, allowed to stand for stratification, added 15g of sodium carbonate aqueous solution with a concentration of 10wt% to the organic layer, stirred for 10 minutes, stood for stratification, The organic layer was precipitated to obtain 27.5 g of 6-iodosaccharin with a content of 95% and a yield of 88.1%.

Embodiment 3）

[0040] The reaction formula of the present embodiment is as follows:

[0041] .

[0042] The concrete method of this embodiment is as follows:

[0043] Add 20g (0.101mol) of 6-aminosaccharin, 17.6g (0.106mol) of potassium iodide, 6.4g (0.107mol) of acetic acid and 100g of toluene into a 500mL reaction bottle, and drop 9.0g (0.101mol) of isopropyl nitrite at about 10°C mol), reacted at 20°C for 2 hours after dropping, then added 20g of water, stirred for 10 minutes, allowed to stand for stratification, added 15g of sodium carbonate aqueous solution with a concentration of 10wt% to the organic layer, stirred for 10 minutes, stood for stratification, The organic layer was precipitated to obtain 26.5 g of 6-iodosaccharin with a content of 95% and a yield of 84.9%.

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Abstract

The invention discloses a preparation method of an intermediate of iodosulfuron-methyl sodium. The intermediate is obtained by performing a reaction on 6-aminosaccharin and potassium iodide in the presence of alkyl nitrite and acetic acid in one step, wherein a molar ratio of the potassium iodide to the 6-aminosaccharin is 1:1 to 1.2:1; a molar ratio of the alkyl nitrite to the 6-aminosaccharin is0.95:1 to 1:1; the alkyl nitrite is ethyl nitrite, isopropyl nitrite, n-butyl nitrite or isoamyl nitrite; and a molar ratio of the acetic acid to the 6-aminosaccharin is 1:1 to 1.2:1. According to the method provided by the invention, the alkyl nitrite is adopted for diazotization, the potassium iodide is added at the same time, so that decomposition and hydrolysis of a diazonium salt can be avoided, and the reaction yield is greatly improved; and the method does not require a large amount of water as a solvent and only adopts a small amount of water to wash an organic layer in the post-treatment, and therefore wastewater produced by adopting the method provided by the invention does not exceed 2 times the weight of the target product.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates, in particular to a preparation method of iodosulfuron-methyl sodium salt intermediate 6-iodine saccharin. Background technique [0002] Iodosulfuron-methyl sodium is a sulfonylurea herbicide developed by Bayer. Iodosulfuron-methyl sodium salt is an acetolactate synthase (ALS) inhibitor. It is mainly manifested in inhibiting the synthesis of valine and isoleucine in organisms, thus hindering cell division and plant growth, and selectively eliminating weeds in rice. Iodosulfuron-methyl sodium salt is used to control broad-leaved weeds and some grass weeds in cereal crop fields such as pigtail, matricaria, windweed, wild oats and bluegrass. [0003] 6-iodosaccharin is an important intermediate for synthesizing iodosulfuron-methyl sodium salt, and the existing 6-iodosaccharin preparation method basically all makes diazonium salt by reacting 6-aminosaccharin with sodiu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/06
CPCC07D275/06
Inventor 邹佩佩陈新于靓万里红孙永辉
Owner 江苏省农用激素工程技术研究中心有限公司
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