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Method for preparing bispyribac sodium and its intermediates

A technology for bispyribacin sodium and sodium salt, which is applied in the field of preparing bispyribacin sodium and its intermediates, and can solve the problems of low yield, slow reaction rate, high impurity content, etc.

Active Publication Date: 2018-05-11
GHARDA CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] However, there are still some defects in the methods for preparing bispyribacin sodium, 4,6-disubstituted-2-alkylsulfonylpyrimidine and 2,6-dihydroxybenzoic acid in the prior art, such as high impurity content, Low yield, slow reaction rate, and low cost-effectiveness

Method used

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  • Method for preparing bispyribac sodium and its intermediates
  • Method for preparing bispyribac sodium and its intermediates
  • Method for preparing bispyribac sodium and its intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] A clear solution of 154 g of 2,6-dihydroxybenzoic acid in 500 ml of dimethyl sulfoxide was added to 130 g of a commercially available solution dissolved in 2 liters of dimethyl sulfoxide over 2-3 hours at 30-32°C. A mixture of sodium hydride (60% oil-based emulsion). The material was further stirred at 30-32°C for 2 hours, and 480 grams of 4,6-dimethoxy-2-(methylsulfonyl)pyrimidine was added over 2 hours. The reaction is maintained at 30-32°C until complete to obtain bispyribac-sodium. The reaction was monitored by high performance liquid chromatography (HPLC). The material was filtered and washed with dimethylsulfoxide (DMSO). Add 1000ml of methanol to the wet solid again to form a slurry, and then add 1000ml of 75% aqueous methanol to form a slurry. The wet solid was dried to obtain 435 g of bispyribac-sodium. The sodium bispyribac was re-slurried in 1200 ml of toluene at reflux temperature, cooled, filtered and dried to obtain 385 g of sodium bispyribac (HPLC pur...

Embodiment 2

[0133] A clear solution of 154 g of 2,6-dihydroxybenzoic acid in 500 ml of dimethyl sulfoxide was added to 130 g of commercially available hydrogenate dissolved in 1500 ml of dimethyl sulfoxide at 30-32°C for 2-3 hours. Sodium (60% Oil Based Emulsion). The material was further stirred at 30-2°C for 2 hours, and 480 grams of 4,6-dimethoxy-2-(methylsulfonyl)pyrimidine was added over 2-3 hours. The reaction is maintained at 30-32°C until complete to obtain bispyribac-sodium. The reaction was monitored by high performance liquid chromatography. The material was filtered and washed with dimethylsulfoxide. Add 1000ml of methanol to the wet solid again to form a slurry, and then add 1000ml of 75% aqueous methanol to form a slurry. The wet solid was dried to obtain 430 g of bispyribac-sodium. The sodium bispyribac was re-slurried in 1200 ml of toluene at reflux temperature, cooled, filtered and dried to obtain 380 g of sodium bispyribac (HPLC purity 98.3%).

Embodiment 3

[0135] A clear solution of 154 g of 2,6-dihydroxybenzoic acid in 500 ml of dimethyl sulfoxide was added at 30-32° C. to 130 g of commercially available sodium hydride (60% oleyl sulfoxide) dissolved in 1500 ml of dimethyl sulfoxide. emulsion) mixture. The mass was stirred for a further 2 hours at 30°C and a slurry of 480 grams of 4,6-dimethoxy-2-(methylsulfonyl)pyrimidine in 750 ml of dimethylsulfoxide was added. The reaction is maintained at 30-32°C until complete to obtain bispyribac-sodium. The material was filtered and washed with dimethylsulfoxide. Add 1000ml of methanol to the wet solid again to form a slurry, and then add 1000ml of 75% aqueous methanol to form a slurry. The wet solid was dried to obtain 440 g of bispyribac-sodium. The sodium bispyribac was re-slurried in 1200 ml of toluene at reflux temperature, cooled, filtered and dried to obtain 380 g of sodium bispyribac (HPLC purity 98.5%).

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Abstract

The present invention relates to a kind of method that is used for preparing bispyribac ether sodium, it is by in the situation that at least one alkali and at least one solvent exist, will 2,6-dihydroxybenzoic acid and 2-(alkylsulfonyl) ‑4,6‑dialkoxypyrimidine for condensation. The present invention also relates to a process for the preparation of 2,6-dihydroxybenzoic acid and 2-(alkylsulfonyl)-4,6-dialkoxypyrimidine.

Description

technical field [0001] The invention relates to a method for preparing bispyribac sodium and an intermediate thereof. Background technique [0002] bispyribac sodium [0003] International Union of Theoretical and Applied Chemistry (IUPAC) Name: Sodium 2,6-bis(4,6-dimethoxypyrimidin-2-yloxy)benzoate [0004] structure: [0005] [0006] Chemical formula: C 19 h 17 N 4 NaO 8 [0007] Molecular weight: 452.4 [0008] Physical state: white powder [0009] Melting point: 223-224°C [0010] Water solubility: 73.3g / l at 25°C [0011] Mode of Action: Selective, systemic post-emergent herbicide, absorbed by stems, leaves and roots. [0012] Bispyribac-sodium is a systemic herbicide that penetrates plant tissue and acts by interfering with the production of the enzyme acetolactate synthase (ALS), which is essential for plant growth. It is used to control weeds, sedges and broadleaf weeds, especially barnyardgrass in direct seeded rice. It is also used to suppress weed...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/60C07D239/30
CPCC07D239/38C07D239/60C07D403/12
Inventor 马图尔·苏切·S维贾扬·安尼努加雷·维纳亚克·H博萨莱·萨钦·R达帕克·芒格舍·K帕卡尔·苏雷什库马尔·D达马尼亚·普拉涅什·D贾格塔普·南丹基肖尔·S卡利拉扬·A坎卡尔·拉胡尔·H贾殷·南丹库马尔·J莫雷·马亨德兰·M阿赫·萨蒂亚万·B帕德瓦尔·萨钦·S
Owner GHARDA CHEM LTD
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