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Synthesis method of thioketone

A synthesis method and thione technology, applied in organic chemistry and other directions, can solve the problems of low equipment utilization rate, low yield, poor product stability, etc., and achieve the effects of high equipment utilization rate, simple operation steps and high stability.

Pending Publication Date: 2022-05-06
德州绿霸精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 8-Fluoro-5-methoxy-2H-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione is an important intermediate in the synthesis of florasulam, and its synthesis reaction It is an oxidation reaction of one of the 18 hazardous processes under key supervision. In the past, 8-fluoro-5-methoxy-2H-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione The synthesis usually uses a kettle reaction, which is dangerous, has low utilization rate of equipment, incomplete reaction, poor product stability, and low yield, so it is not suitable for industrial production.

Method used

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  • Synthesis method of thioketone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis method of 8-fluoro-5-methoxy-2H-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione in this example has the following steps:

[0029] (1) Transfer 1400Kg of dry methanol into the 3000L reactor through a flow meter, open the manhole and put in 600Kg of 5-fluoro-4-hydrazino-2-methoxypyrimidine, heat up to 30°C, stir for 1 hour to completely dissolve and set aside , to detect the content of 5-fluoro-4-hydrazino-2-methoxypyrimidine;

[0030] (2) The reaction temperature of the microchannel reactor I is set to 50 DEG C, and the two channels of the microchannel reactor I are transported with 5-fluoro-4-hydrazino-2-methoxypyrimidine and Carbon disulfide, adjust the flow rate of the diaphragm metering pump to ensure that the mol ratio of 5-fluoro-4-hydrazino-2-methoxypyrimidine to carbon disulfide is 1:1.1, and the residence time of the material in the microchannel reactor I is 5min. After completion, the feed liquid enters the intermediate storage tank for use;

[0031] ...

Embodiment 2

[0034] The synthesis method of 8-fluoro-5-methoxy-2H-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione in this example has the following steps:

[0035] (1) Transfer 1400Kg of dry chloroform into a 3000L reactor through a flow meter, open the manhole and put in 600Kg of 5-fluoro-4-hydrazino-2-methoxypyrimidine, heat up to 30°C, stir for 1 hour to completely dissolve and set aside , to detect the content of 5-fluoro-4-hydrazino-2-methoxypyrimidine;

[0036] (2) The reaction temperature of the microchannel reactor I is set to 60 DEG C, and the two channels of the microchannel reactor I are transported with 5-fluoro-4-hydrazino-2-methoxypyrimidine and Carbon disulfide, adjust the flow rate of the diaphragm metering pump to ensure that the mol ratio of 5-fluoro-4-hydrazino-2-methoxypyrimidine to carbon disulfide is 1:1.2, and the residence time of the material in the microchannel reactor Ⅰ is 6min. After completion, the feed liquid enters the intermediate storage tank for use;

[0037] ...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of 8-fluoro-5-methoxy-2H-[1, 2, 4] triazolo [4, 3-c] pyrimidine-3-thioketone, which comprises the following steps: (1) dissolving 5-fluoro-4-hydrazino-2-methoxypyrimidine in a solvent for later use; (2) putting hydrogen peroxide into a storage tank for later use; (3) putting carbon disulfide out of the storage tank for later use; (4) at a certain temperature, respectively pumping the 5-fluoro-4-hydrazino-2-methoxypyrimidine solution and carbon disulfide into the micro-channel reactor I by using a diaphragm metering pump, and completing the reaction; (5) pumping hydrogen peroxide into the micro-channel reactor II by using a diaphragm metering pump, and completing the oxidation reaction; and (6) centrifuging the reaction material liquid through a centrifugal machine to obtain a 8-fluoro-5-methoxy-2H-[1, 2, 4] triazolo [4, 3-c] pyrimidine-3-thioketone solution. The method has the advantages of simple operation steps, low risk, high equipment utilization rate, complete reaction, high product stability and high yield.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, specifically a method for synthesizing 8-fluoro-5-methoxy-2H-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione . Background technique [0002] Flosulam is a triazolopyrimidine sulfonamide herbicide developed by Dow Agricultural Sciences Company of the United States. Its mechanism of action is to inhibit the synthesis of acetolactate synthase, thereby preventing the synthesis of related amino acids. Plants cannot synthesize proteins and die . Flusulam is a broad-spectrum herbicide with high efficiency and low toxicity for controlling broad-leaved weeds in post-emergence stem and leaf treatment. [0003] 8-Fluoro-5-methoxy-2H-[1,2,4]triazolo[4,3-c]pyrimidine-3-thione is an important intermediate in the synthesis of florasulam, and its synthesis reaction It is an oxidation reaction of one of the 18 hazardous processes under key supervision. In the past, 8-fluoro-5-methoxy-2H-[1,2,4]triazolo[4,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 田俊杰朱恒营索存川季云飞张海刘振兴
Owner 德州绿霸精细化工有限公司
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