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Preparation method for 2-amino sulfonyl-4-methylsalfonamido methyl benzoic acid methyl ester

A technology of methyl sulfonyl amidomethyl benzoate and methyl sulfonyl amido methyl toluene, applied in the field of preparation of pesticide intermediates, can solve the problems of high risk, only 32% total yield, high price, etc. Achieve the effect of optimizing reaction conditions, shortening synthetic route and improving reaction yield

Active Publication Date: 2014-04-30
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

The disadvantages of this method are: (1) the raw material 4-cyano-2-nitrobenzoic acid methyl ester is expensive and not easy to obtain; (2) the reduction reaction needs to be carried out under a high pressure of 1700kPa, and the operation is more dangerous; (3) the synthesis The route is long and not suitable for industrial production; (4) The total yield is only about 34%
The disadvantages of this method are: (1) the raw material N-tert-butyl-2-methoxycarbonyl-5-methylbenzenesulfonamide is not easy to obtain; (2) the highly dangerous sodium azide reagent is used; (3) The synthetic route is long and not suitable for industrial production; (4) The total yield is only about 21%
The disadvantages of this method are: (1) The synthetic route is long and not suitable for industrial production; (2) The total yield is only about 32%.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0028] The present embodiment prepares the intermediate product 2-aminosulfonyl-4-methylsulfonylaminomethyltoluene through the chlorosulfonation-ammonolysis reaction of p-methylsulfonamidomethyltoluene, and the steps are as follows:

[0029] ①Dissolve 200g of p-methylsulfonamidomethyltoluene (1.0mol) in 600mL of 1,2-dichloroethane, cool down to -5±1°C in an ice bath, and drop in 468g of chlorosulfonic acid ( 4.0mol), the temperature was raised to reflux to carry out chlorosulfonation reaction until the reaction was complete.

[0030] ② After the reaction is over, first distill off the 1,2-dichloroethane solvent and excess chlorosulfonic acid under reduced pressure, then add the reaction material to ice water at -5±1°C, precipitate solids, filter with suction, and filter the cake through After washing, it was added to 500 mL of ammonia water with a concentration of 27 wt%, and stirred at room temperature for ammonolysis reaction until the reaction was complete.

[0031] ③After...

Embodiment 2～ Embodiment 6）

[0033] The method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0034] Table 1

[0035] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 p-methylsulfonamidomethyltoluene 200g 200g 200g 200g 200g 200g solvent 1,2-Dichloroethane 1,2-Dichloroethane 1,2-Dichloroethane Dichloromethane 1,2-Dichloroethane 1,2-Dichloroethane Chlorosulfonic acid 468g 468g 468g 468g 350g 582g Adding temperature of chlorosulfonic acid -5±1℃ -2±1℃ -8±1℃ -5±1℃ -5±1℃ -5±1℃ ice water temperature -5±1℃ -2±1℃ -8±1℃ -5±1℃ -5±1℃ -5±1℃ 2-Aminosulfonyl-4-methanesulfonylamidomethyltoluene weight 227.5g 223.0g 224.5g 222.7g 224.2g 224.9g purity 92% 93% 91% 90% 91% 90% yield 75.3% 74.6% 73.5% 72.1% 73.4% 72.8%

Embodiment 7）

[0037] The present embodiment also prepares the intermediate product 2-aminosulfonyl-4-methanesulfonamidomethyl toluene by p-methylsulfonyl amidomethyltoluene through chlorosulfonation-ammonolysis reaction, and has the steps as follows:

[0038] ① Add 200g of p-methylsulfonamidomethyltoluene (1.0mol) into the reaction device, cool down to -5±1°C in an ice bath, add 468g of chlorosulfonic acid (4.0mol) dropwise under stirring, and raise the temperature to Chlorosulfonation reaction was carried out at 80°C±1°C until the reaction was complete.

[0039] ② After the reaction is over, first remove the excess chlorosulfonic acid under reduced pressure, then add the reaction material into ice water at -5±1°C, precipitate the solid, filter it with suction, and add the filter cake to 500mL of 27wt% chlorosulfuric acid after washing Ammonia solution was stirred at room temperature for ammonolysis reaction until the reaction was complete.

[0040] ③ After the reaction, filter with suctio...

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PUM

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Abstract

The invention discloses a preparation method for 2-amino sulfonyl-4-methylsalfonamido methyl benzoic acid methyl ester. According to the preparation method, sulfonamide methyl toluene is used as raw material and subjected to chlorosulfonation-ammonolysis reaction, oxidation reaction and methanolysis reaction to prepare the2-amino sulfonyl-4-methylsalfonamido methyl benzoic acid methyl ester, wherein in the chlorosulfonation reaction, sulfonamide methyl toluene and organic solvents are added to a reaction device to be cooled to minus 10 DEG C-0 DEG C via an ice bath, then chlorosulfonation reagents are dropwise added, next the mixtures are heated till reflux occurs and the reaction is complete. The preparation method disclosed by the invention can prepare 2-amino sulfonyl-4-methylsalfonamido methyl benzoic acid methyl ester by using sulfonamide methyl toluene as raw material via three reaction steps, greatly shortens the synthetic process, and is quite suitable for commercial process. The overall yield can reach above 50% by optimizing the chlorosulfonation-ammonolysis reaction condition.

Description

technical field [0001] The invention relates to a preparation method of a pesticide intermediate, in particular to a preparation method of 2-aminosulfonyl-4-methanesulfonamidomethylbenzoate. Background technique [0002] Mesosulfuron-methyl is a newly developed sulfonylurea super-efficient herbicide in recent years, and 2-aminosulfonyl-4-methanesulfonamidomethylbenzoate is one of the preparations of mesosulfuron-methyl. key intermediates. [0003] Chinese patent document CN1443159A discloses a kind of 4-cyano-2-nitrobenzoic acid methyl ester as raw material, followed by high-pressure hydrogenation reaction, mesylation reaction, diazotization / sulfonyl chloride reaction, ammoniation reaction to prepare Methyl 2-aminosulfonyl-4-methanesulfonamidomethylbenzoate was obtained. The disadvantages of this method are: (1) the raw material 4-cyano-2-nitrobenzoic acid methyl ester is expensive and not easy to obtain; (2) the reduction reaction needs to be carried out under a high pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/37C07C303/40
Inventor 孔繁蕾张璞周荣华吴溧明刘晓佳陈新
Owner 江苏省农用激素工程技术研究中心有限公司
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