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Synthetic method of 2-(4,6-dimethylpyrimidine-2-ylamidoformamidosulfonyl)methyl benzoate

A technology of methyl carbamoylsulfamoyl and o-methoxycarbonylbenzenesulfonyl formate, applied in the field of synthesis of methyl 2-benzoate, can solve severe corrosion, high equipment requirements, large pollution and corrosion, etc. problems, to achieve the effects of avoiding safety accidents, good purity, and reducing production costs

Active Publication Date: 2014-01-08
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 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-dimethylpyrimidine-2-ylamidoformamidosulfonyl)methyl benzoate
  • Synthetic method of 2-(4,6-dimethylpyrimidine-2-ylamidoformamidosulfonyl)methyl benzoate
  • Synthetic method of 2-(4,6-dimethylpyrimidine-2-ylamidoformamidosulfonyl)methyl benzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1) First, add o-benzoylsulfonimide (saccharin) (20g, 0.11mol), 70mL of methanol, and 98% concentrated sulfuric acid (2g, 0.02mol) into a 250mL three-necked flask, heat and reflux for 3 hours, and then Concentrate under reduced pressure to remove methanol, wash with water until neutral, filter, and dry to obtain 21.7 g of intermediate o-methoxycarbonylbenzenesulfonamide with a content of 98% and a yield of 90%. mp: 122-124°C.

[0040] IR (cm -1 ): 3338, 3235, 3093, 2953, 1716, 1590, 1600, 1557, 1337, 1270, 1161.

[0041] 1 H NMR (δ ppm): 3.84 (3H, s), 7.30 (2H, s), 7.70 (3H, m), 7.98 (1H, d).

[0042] 2) Raise the temperature to 70°C-75°C, under the protection of nitrogen, add o-methoxycarbonylbenzenesulfonamide (21.5g, 0.1mol) and sodium methoxide (21.6g, 0.12mol) into the three-necked flask, and then add carbonic acid dropwise Dimethyl ester (10.8g, 0.12mol) was refluxed for 8 hours, then the solvent was distilled off, the temperature was lowered to below 40°C, and...

Embodiment 2

[0050] 1) Add saccharin (20g, 0.11mol), 30mL of methanol, and concentrated sulfuric acid (2.0g, 0.02mol) into a 250mL three-neck flask, heat to reflux for 3 hours, cool to below 10°C, and slowly add sodium methoxide solution (26.0g, 0.143mol), heat up to 70℃~75℃ for 2h, then add dimethyl carbonate (10.8g, 0.12mol) dropwise within 1h, then reflux for 8h, then distill off the solvent, add 50ml of water after cooling down, and finally use mass The hydrochloric acid with a concentration of 5% was neutralized to neutral, filtered and dried to obtain 24.8 g of methyl o-methoxycarbonylbenzenesulfonamide formate, the content was 98%, and the yield was 81%.

[0051] 2) After adding 100ml of DMF, methyl o-methoxycarbonylbenzenesulfonamide formate (13.7g, 0.05mol) and 4,6-dimethylpyrimidinamine (6.15g, 0.05mol) into a three-neck flask, heat to 100°C-105°C, react for 16h; evaporate the solvent under reduced pressure, cool to room temperature, add water to the bottle, filter, wash with wat...

Embodiment 3

[0054] The difference between this example and Example 1 is that the catalyst A used in the step (1) is sodium bisulfate. The corresponding yields are shown in Table 1.

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Abstract

The invention discloses a synthetic method of 2-(4,6-dimethylpyrimidine-2-ylamidoformamidosulfonyl)methyl benzoate. The synthetic method comprises the following steps of: reacting saccharin with methanol to prepare an intermediate methyl 2-sulfamoylbenzoate, and then preparing an intermediate methyl 2-sulfamoylbenzoate methyl formate from dimethyl carbonate and sodium methoxide with methanol and the like as a solvent. The 2-(4,6-dimethylpyrimidine-2-ylamidoformamidosulfonyl)methyl benzoate prepared by the synthetic method provided by the invention has the purity of more than 95.0% and the total yield of more than 65.0%. The preparation method provided by the invention has the advantages of cheap and easy-to-get raw materials, simple process, few three wastes, avoidance of virulent suffocating gas, applicability to batch industrial production and the like.

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, Arabian sorghum, ragweed, etc. The dosage is 210-250g / h m, which can be sprayed conventionally or by aircraf...

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徐泽刚刘军张晓光林双政孙侨南王安勇陈涛刘康云
Owner XIAN MODERN CHEM RES INST
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