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Synthetic method of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate

A technology of methyl carbamoylaminosulfonyl and o-methoxycarbonylbenzenesulfonamidomethyl formate, applied in the field of synthesis of 2-benzoic acid methyl ester, can solve the problem of easy hydrolysis and deterioration, hidden dangers of environmental protection and safety, environmental pollution, etc. problems, to achieve the effect of easy control of reaction conditions, avoidance of safety accidents, and reduction of production costs

Active Publication Date: 2014-01-01
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this kind of method still has some problems such as environmental pollution and high cost, take the disclosed method of US2362648 as example:
[0010] One, one of the raw materials used during the preparation of the intermediate o-methoxycarbonylbenzenesulfonyl isocyanate is phosgene, which is a highly toxic chemical, pollutes the environment when used, and also has environmental safety hazards
[0011] Second, the intermediate o-methoxycarbonylbenzenesulfonyl isocyanate has poor stability, is easily hydrolyzed and deteriorated, and the product quality is difficult to control
[0012] Third, the intermediate o-methoxycarbonylbenzenesulfonyl isocyanate is severely corroded during the preparation process, requiring high equipment, and the preparation process is highly polluted and corroded

Method used

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  • Synthetic method of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate
  • Synthetic method of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate
  • Synthetic method of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) First, add saccharin (20g, 0.11mol), sodium methoxide (21.6g, 0.12mol) and methanol 100ml into a 250mL three-neck flask, heat to 70-75°C, and then dropwise add dimethyl carbonate (10.8g, 0.12mol) reflux reaction for 8.5h, then distilled off the solvent, lowered the temperature to below 40°C and added 80ml of water, and finally neutralized to neutral with 5% hydrochloric acid by mass percentage, filtered and dried to obtain 24.3g of N-methyl formate-phthalic acid Acylsulfonimide, content 98%, yield 90.0%.

[0041] IR (cm -1 ): 3090, 1793, 1742, 1588, 1362, 1187;

[0042] 1 H NMR (δppm): 3.63 (3H, s), 7.61 (1H, t), 7.85 (1H, t), 8.02 (1H, d), 8.41 (1H, d);

[0043] (2) Add 100ml of methanol, N-methyl formate-o-benzoylsulfonimide (12.1g, 0.05mol) and hydrochloric acid (5.0g) into a three-neck flask, heat to reflux for 1.5h, concentrate under reduced pressure and evaporate Methanol, washed with water until neutral, filtered, and dried to obtain 12.5 g of methyl o-me...

Embodiment 2

[0051] The difference between this embodiment and embodiment 1 is that steps (1) and (2) are combined:

[0052] Add saccharin (20g, 0.11mol), sodium methoxide (21.6g, 0.12mol) and methanol 100ml into a 250mL three-neck flask, heat to 70-75°C, then add dropwise dimethyl carbonate (10.8g, 0.12mol) to reflux reaction After 8.5h, the solvent was evaporated to dryness, 80ml of methanol and hydrochloric acid (2.5g) were added under cooling, and the reaction was heated to reflux for 1.5h. The methanol was evaporated by concentration under reduced pressure, washed with water, filtered, and dried to obtain 24.4g of o-methoxycarbonylbenzenesulfonamide Methyl formate, content 95%, yield 85%.

Embodiment 3

[0054] The difference between this example and Example 1 is that catalyst A in step (1) is sodium hydroxide 6g (0.15mol), and the yield of N-methyl formate-o-benzoylsulfonimide in step (1) 85%.

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Abstract

The invention discloses a synthetic method of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate. The method is characterized in that gluside and dimethyl carbonate are adopted for preparing an intermediate of N-methyl formate-o-sulfonylbenzoylimine, and then methanol is adopted for preparing an intermediate of o-methoxy carboxide benzenesulfonamide methyl formate. The purity of 2-(4,6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate prepared by the synthetic method provided by the invention reaches more than 95.0%, and the total yield reaches 55.0%. The method is mainly applied to preparation of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate and has the advantages that raw materials are cheap and easy to obtain, the technology is simple, the three wastes are few, virulent suffocating gas is prevented from being used, and the method is suitable for batch industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing methyl 2-(4,6-dimethylpyrimidin-2-ylcarbamoylsulfonyl)benzoate. Background technique [0002] Sulfonylurea herbicides inhibit the synthesis of branched-chain amino acids, thereby inhibiting cell division at the growing end of plants and preventing weeds from growing to chlorosis and necrosis. The structural formula of methyl 2-(4,6-dimethylpyrimidin-2-ylcarbamoylsulfonyl)benzoate is shown in Formula I. [0003] [0004] It is a pre-emergence and post-emergence herbicide, which is suitable for controlling annual and perennial grass weeds and broad-leaved weeds in trees, or opening up forest isolation belts, clearing forest land after logging, wasteland before reclamation, leisure non-arable land, and roadsides Weeding and irrigation in wasteland, such as fescue, goldenrod, millet, oil sedge, ara [0005] Sorghum sorghum, ragweed, etc. The dosage is 210-250g / h m, which can be sprayed conventionally...

Claims

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Application Information

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IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 王列平宁斌科钱一石黄晓瑛张晓光刘军徐泽刚林双政张建功孙侨南王威刘康云
Owner XIAN MODERN CHEM RES INST
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