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Synthesis method of rimsulfuron

A synthesis method and technology of rimsulfuron-methyl, applied in the field of herbicide synthesis, can solve the problems of low yield, existence of impurities, low yield and the like, and achieve the effects of high purity, few impurities and improved purity

Pending Publication Date: 2020-09-11
绍兴上虞新银邦生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The 2-fluoropyridine synthesis route has harsh reaction conditions, low yield, and the raw materials and reagents used are relatively expensive, so it is not suitable for industrial production
The ring-closing synthetic pyridine synthesis route is simple, but the yield is not high, and there are impurities, resulting in low purity of rimsulfuron-methyl, so it is urgent to provide a synthetic method for rimsulfuron-methyl with higher purity

Method used

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  • Synthesis method of rimsulfuron
  • Synthesis method of rimsulfuron
  • Synthesis method of rimsulfuron

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] refer to figure 1 , a synthetic method of rimsulfuron-methyl, comprising the steps of:

[0032] S1: Raw material preparation. Prepare 3-ethanesulfonyl-2-ethanesulfonamidopyridine and 4,6-dimethoxypyrimidine-2-carbamate phenyl ester.

[0033] Preparation of 3-ethanesulfonyl-2-ethanesulfonamidopyridine:

[0034] First add 20kg of water, 10kg of hydrochloric acid and 54kg of dichloromethane into the first container, then add 18kg of 3-ethanesulfonyl-2-mercaptopyridine, start stirring, and at the same time reduce the temperature in the first container to 4°C and keep warm 3min. Then start dripping sodium hypochlorite, the dripping amount of sodium hypochlorite is 170kg, and the dropping temperature is 13 ℃, after dropping, it is incubated for 15min, then drips ammoniacal liquor in the organic phase, and the dripping amount of ammoniacal liquor is 36kg, and the sampling analysis ammonia transformation rate is After the concentration is above 85%, hydrochloric acid is add...

Embodiment 2

[0046] The difference from Example 1 is that S3: purification. Including the following steps:

[0047] A. Weigh 20kg of the rimsulfuron-methyl crude product obtained in S2, add it to the first solvent, heat it to 70°C under stirring, and keep it warm for 3h; the first solvent is 40kg, and then heat the liquid system to 30°C for 10h. The first solvent is chloroform.

[0048] B. Add a second solvent to the liquid treated in step A, then cool the liquid system to 5°C, then filter the precipitate, and take the filter cake for later use; the amount of the second solvent added is 20kg; the second solvent is octane.

[0049] C. Add the filter cake obtained in step B into the third solvent, stir and beat, and keep the beating temperature at 25° C. for 4 hours; the amount of the third solvent added is 16 kg; the third solvent is anisole.

[0050] D. Filtering and drying the substance treated in step C to obtain the original drug of rimsulfuron-methyl.

Embodiment 3

[0052] The difference from Example 1 is that S3: purification. Including the following steps:

[0053] A. Weigh 20kg of the rimsulfuron-methyl crude product obtained in S2, add it to the first solvent, heat it to 70°C under stirring, and keep it warm for 3h; the first solvent is 40kg, and then heat the liquid system to 30°C for 10h. The first solvent is carbon tetrachloride.

[0054] B. Add a second solvent to the liquid treated in step A, then cool the liquid system to 5°C, then filter the precipitate, and take the filter cake for later use; the amount of the second solvent added is 20kg; the second solvent is toluene.

[0055] C. Add the filter cake obtained in step B into the third solvent, stir and beat, and keep the beating temperature at 25°C for 4 hours; the amount of the third solvent added is 16kg; the third solvent is methyl tert-butyl ether .

[0056] D. Filtering and drying the substance treated in step C to obtain the original drug of rimsulfuron-methyl.

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Abstract

The invention relates to the technical field of herbicide synthesis, and discloses a rimsulfuron synthesis method, which comprises the following steps of: S1, preparation of raw materials; S2, condensation; and S3, purification: A, adding a rimsulfuron crude product obtained in S2 into a first solvent, heating to 40-100 DEG C, and keeping the temperature for 2-5 hours, wherein the mass ratio of the rimsulfuron crude product to the first solvent is 1: 2; B, adding a second solvent into the liquid treated in the step A, then cooling a liquid system to -10 to 20 DEG C, then filtering precipitates, and taking a filter cake for later use, wherein the mass ratio of the second solvent to the first solvent in the step A is 1: 2; C, adding the filter cake obtained in the step B into a third solvent, stirring and pulping, and keeping the pulping temperature at 0-50 DEG C for 2-6 hours, wherein the mass ratio of the third solvent to the first solvent in the step A is 1: 2.5; and D, filtering anddrying the substance treated in the step C to obtain the rimsulfuron active compound. The purity of the finally prepared rimsulfuron can be improved.

Description

technical field [0001] The invention relates to the technical field of herbicide synthesis, more specifically, it relates to a synthesis method of rimsulfuron-methyl. Background technique [0002] 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pyridylsulfonyl)urea is rimsulfuron-methyl, the molecular formula is C 14 h 17 N 5 o 7 S 2 , is a powerful herbicide, also known as rimsulfuron-methyl, trade name Baocheng. Rimisulfuron-methyl is a sulfonylurea herbicide variety developed by DuPont Company of the United States. It has the advantages of high selectivity, high efficiency, and low toxicity. It is an important herbicide for corn fields. The drug is an amino acid compound inhibitor that stops cell differentiation and plant growth by inhibiting the biosynthesis of essential valine and isoleucine. Absorbed by roots and leaves, it is quickly transmitted to meristems. The drug is effective against most and perennial weeds in cornfields and can also be used on potat...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 刘胜学史银涛
Owner 绍兴上虞新银邦生化有限公司
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