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Synthetic method of bupirimate

A technology of pyrimethamine sulfonate and synthesis method, applied in directions such as organic chemistry, can solve problems such as complicated operation, and achieve the effect of reducing operation steps and production cost

Active Publication Date: 2020-06-19
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above-mentioned improved process still has the problem that the solvent in the reaction needs to be refluxed for water separation, and the operation is complicated

Method used

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  • Synthetic method of bupirimate
  • Synthetic method of bupirimate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 20.9g of pyrimol, 13.9g of potassium carbonate, 180ml of toluene, 1.8ml of water, and 0.01% of 18-crown-6 into the reaction flask in sequence, raise the temperature to 70°C under stirring, and slowly add 14.4g of N,N-dimethyl Sulfonyl chloride, after dropping, the temperature was raised to reflux for 2 hours, and triethylamine was added dropwise to control the pH of the system to 9 when 50% of the remaining raw materials were detected, and the reaction was continued for 4 hours until the end. Then the system was cooled to 55°C, washed with water to adjust the system to neutral, the water phase was separated, and the solvent was removed to obtain an oily substance. The solid was precipitated at a low temperature of 10°C, dried and weighed 29.4g, which was pyrimetholsulfonate .

[0031] Yield 93%, content 98%.

[0032] 1 HNMR(500MHz,DMSO):δ0.9(t,3H),1.13(t,3H),1.2~1.5(m,4H),2.3(s,3H),2.4(t,3H),2.9(s, 6H), 3.2(m,2H), 7.16(s,1H); IR(KBr,cm -1 ):3420,2960,2875,2858,1...

Embodiment 2

[0035] Add 20.9g of pyrimol, 15.9g of sodium carbonate, 180ml of toluene, 0.18ml of water, and 0.1% tetramethylammonium bromide into the reaction flask in sequence, raise the temperature to 70°C under stirring, and slowly add 17.3g of N,N-di Methanesulfonyl chloride, after dropping, the temperature was raised to reflux for 2 hours, and an equal amount of triethylamine was added to control the pH of the system to 10 when the remaining 15% of raw materials were detected, and the reaction was continued for 3 hours until the end. Then the system was cooled to 60°C, washed with water to adjust the system to neutral, the water phase was separated, and the oil was obtained after removing the solvent. The solid was precipitated at a low temperature to 0°C, dried and weighed 29.4g, which was pyrimetholsulfonate , yield 93%, content 97%.

Embodiment 3

[0037] Add 20.9g of pyrimol, 10.6g of sodium carbonate, 180ml of benzene, 2ml of water, and 0.05% tetramethylammonium chloride into the reaction flask in sequence, raise the temperature to 75°C under stirring, and slowly add 14.4g of N,N-dimethyl Sulfonyl chloride, after dropping, the temperature was raised to reflux for 2 hours. When 5% of the raw material was detected, an equal amount of pyridine was added to control the pH of the system to 9, and the reaction was continued for 1 hour until the end. Then the temperature of the system was lowered to 50°C, washed with water to adjust the system to neutral, the water phase was separated, and the oil was obtained after the solvent was removed. The solid was precipitated at a low temperature of 10°C, dried and weighed 29.5g, which was pyrimetholsulfonate , yield 93.5%, content 97%.

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Abstract

The invention discloses a synthetic method of bupirimate. The synthetic method comprises the following steps of sequentially adding ethirimol, alkali, a solvent and water into a reaction bottle, heating to 50-80 DEG C while stirring, slowly dropwise adding N, N-dimethylsulfonyl chloride, heating until reflux reaction after finishing dropwise adding, adding organic alkali to control the pH value ofthe system to be alkaline when 5-50% of the raw materials are left, and continuously reacting until the reaction is finished, and cooling the system to 50-60 DEG C, washing with water to adjust the system to be neutral, removing the water phase, removing the solvent to obtain an oily substance, and separating out a solid at low temperature, thereby obtaining the bupirimate. The synthetic method provided by the invention has the advantages of mild conditions, simple operation, less three wastes and high yield, and is a synthetic method suitable for industrialization of bupirimate.

Description

technical field [0001] The invention belongs to the field of pesticide synthesis, and in particular relates to a method for synthesizing pyrithrimol sulfonate. [0002] technical background [0003] Pyrimidine sulfonate is a pyrimidine fungicide invented by the British Imperial Chemical Industries Company. It has the characteristics of high efficiency, low toxicity and good environmental compatibility. It belongs to the inhibitor of adenine nucleosine deaminase and is a systemic fungicide. , can be quickly absorbed by the roots, stems, and leaves of plants, and circulate to various parts of the plant body. It has protective and therapeutic effects, and is mainly used to prevent and control the powdery mildew of economic crops and ornamental plants such as apples, pears, strawberries, and greenhouse roses. [0004] Literature reports (DE2246645 / DE2265028 / DE2265312 and Li Jingxia, optimization of pyrithrimol sulfonate synthesis process, "Journal of Sanmenxia Vocational and Tech...

Claims

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Application Information

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IPC IPC(8): C07D239/47
CPCC07D239/47Y02P20/584
Inventor 王威王列平刘康云黄晓瑛郑晓蕊宁斌科薛超
Owner XIAN MODERN CHEM RES INST
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