CN102372702A - Preparation method for thiamethoxam - Google Patents
Preparation method for thiamethoxam Download PDFInfo
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- CN102372702A CN102372702A CN2011103643998A CN201110364399A CN102372702A CN 102372702 A CN102372702 A CN 102372702A CN 2011103643998 A CN2011103643998 A CN 2011103643998A CN 201110364399 A CN201110364399 A CN 201110364399A CN 102372702 A CN102372702 A CN 102372702A
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Abstract
The invention relates to a preparation method for thiamethoxam. The preparation method comprises the following specific steps of: dissolving 3-methyl-4-nitroimidotetrahydro-1,3,5-oxadiazine and 2-chlorine-5-chloromethyl thiazole into a polar aprotic organic solvent, adding potassium iodide serving as a catalyst and potassium carbonate serving as an acid binding agent, stirring at normal temperature or in a heating way for 8 hours, and detecting whether reaction is fully completed through TLC (Thin Layer Chromatography), wherein a reaction system always keeps in yellow suspension state; and evaporating the organic solvent out, adding methylene dichloride into residues for immersion cleaning, filtering inorganic salts out, obtaining an organic phase which is a deep yellow transparent solution, evaporating the methylene dichloride to dryness, and recrystallizing the crude product by using methylbenzene to obtain maize-yellow thiamethoxam, wherein the yield is 85 percent and the purity is 98 percent. The preparation method has the advantages: the affinity substitution process is stable and quick, the tendency of a side reaction is lowered greatly, the bottleneck of the requirement on the purity of the 2-chlorine-5-chloromethyl thiazole is overcome, the problem of black color of the product is solved completely, and the product yield is greatly increased.
Description
Technical field
The invention belongs to the sterilant preparing technical field, be specifically related to the preparation method of thiophene worm piperazine.
Background technology
The chemical name of thiophene worm piperazine is 3-(2-chloro-1,3-thiazoles-5-ylmethyl)-5-methyl isophthalic acid, 3, and 5-oxadiazines-4-base fork (nitro) amine; Molecular formula C8H10ClN5O3S; Molecular weight 291.71; Be mainly used in lepidopteran, Coleoptera, Thysanoptera insect.Control like various aphids, leafhopper, aleyrodid, plant hopper etc.
By compound 3-methyl-4-nitro-imine base tetrahydrochysene-1,3, the method that 5-oxadiazine and 2-chloro-5-5-chloromethyl thiazole prepare thiophene worm piperazine is by widespread reports, PCT2002034734,2006Mu00715, WO0100623.
But, the color of product, side reaction, and final low yield is the huge obstacle in the industriallization of this step reaction, compd B synthetic with purify relatively easy, compd A synthetic and purify and often this step has been reacted crucial effects.In order to overcome these obstacles, US2004054189 has proposed the scheme of optimizing the most so far, promptly uses feasible method to obtain high-purity compd A (99% purity; Yield 69%), prepares thiophene worm piperazine with this highly purified A again, obtain the product of cream colour at last; Yield 77-78%, content 98-99%.Really; US2004054189 has had a lifting that improves greatly with yield before for the method for purification compd A: previous method requires salify, alkalization release, frozen recrystallization or the like step; Yield is also very low; The thiophene worm piperazine product colour that this method obtains is more shallow, the higher 77-78% of yield, the product of the better 98-99% of purity.
But above-mentioned these existing patented processs; Its obvious defects is: at first, the preparation of thiophene worm piperazine is subject to the purity of compd A all the time, in industrialized process; The operational cycle major part consumes in the purification to compd A, and the long operational cycle has also weakened the stability of compd A greatly; Secondly, 69% compd A yield and 78% thiophene worm piperazine yield certainly will promote the cost of the finished product greatly, have also caused a large amount of three waste discharges.
Summary of the invention
In order to overcome the bottleneck that reaction requires for the compd A high purity; Promote product yield, quality, reduce cost, certainly will will seek a kind of catalyzer and reaction system: on the one hand under this system; Dipole solvent system neutral and alkali a little less than, compd A is degenerated easily; On the other hand, the low solvation inducing action that causes owing to the solvent polarity that reduces, and under the enough strong situation of hypoalkalinity, find a kind of catalyzer can reduce affine substituted activation energy greatly, guarantees that reaction carries out fully to the right; So the present invention provides a kind of preparation method of new thiophene worm piperazine.
The technical solution that realizes above-mentioned purpose is following:
The preparation method of thiophene worm piperazine, concrete operations are following:
Get 3-methyl-4-nitro-imine base tetrahydrochysene-1,3,5-oxadiazine and 2-chloro-5-5-chloromethyl thiazole are dissolved in the organic solvent of aprotic, polar; Add catalyzer potassiumiodide and acid binding agent salt of wormwood; Stirring at normal temperature 8h, the TLC detection reaction is complete, and reaction system keeps yellow outstanding turbid attitude always; Boil off organic solvent, be cooled to room temperature, add methylene dichloride in the residuum and embathe, filter and remove inorganic salt; Intercepting organic phase, organic phase are the deep yellow clear solution, room temperature evaporate to dryness methylene dichloride, and thick product is with the toluene recrystallization; Obtain beige thiophene worm piperazine, amount to yield 84%, purity 98%;
The quality of said catalyzer potassiumiodide is the 1-5% of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said acid binding agent salt of wormwood is 0.6-1 a times of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said organic solvent is 5-20 a times of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said methylene dichloride is 10-30 a times of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said toluene is 5-20 a times of 2-chloro-5-5-chloromethyl thiazole quality.
The organic solvent of said aprotic, polar is acetone or acetonitrile.
Get 18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3,5-oxadiazine and 16.8g2-chloro-5-5-chloromethyl thiazole are dissolved in 180g acetone or the acetonitrile; Add the 0.4g potassiumiodide, 11g salt of wormwood, stirring at normal temperature 8h; The TLC detection reaction is complete, and this moment, reaction system kept yellow outstanding turbid attitude always; 20～55 ℃ of temperature, time 8～12h is cooled to room temperature, and temperature 40-70 ℃ boils off solvent acetone or acetonitrile; Add the 400g methylene dichloride in the residuum and embathe, filter and remove inorganic salt, filtrating is organic phase, and organic phase is the deep yellow clear solution; 35～40 ℃ of evaporate to dryness methylene dichloride of temperature get thick product, and thick product by heating to boiling is cooled to room temperature with 130g toluene recrystallization; Obtain beige thiophene worm piperazine, amount to yield 84%, purity 98%.
The TMAH of catalyzer potassiumiodide contrast US2004054189 report of the present invention; TMAH is forced to accomplish through the strong basicity of self and is tied up acid; Reduce the activation energy of entire reaction; Potassiumiodide through with compd A in active chlorine atom accomplish exchange, iodide ion reduces the activation energy of entire reaction with the intensive leavings group in affine replacement subsequently, so catalytic effect more relaxes.Compd A with 95% purity is a starting raw material, and in some dipole solvents, potassiumiodide can obtain the very light thiophene worm piperazine product of color as catalyzer, and other systems of report are had to the brownish black product.Obviously, potassiumiodide has solved US2004054189 as catalyzer does not have the basic problem that solves; Simultaneously, do not add potassiumiodide and do the acetone of catalyzer, acetonitrile system, backflow 24h also reacts hardly, and after adding the potassiumiodide of catalytic amount, reaction is almost carried out on earth very soon.
For choice of Solvent, be mainly polar aprotic solvent, be preferably acetone, acetonitrile.In the acetone system, the system of not adding potassiumiodide and be catalyzer under refluxad, 24h still carries out slowly; The potassiumiodide system that adds catalytic amount, reaction are at room temperature well carried out in the 8h; Under the equal conditions, system is changed and is made TMAH, Tetrabutyl amonium bromide etc. as catalyzer, and sluggish is carried out or can not be carried out, but reaction system blackening.
The present invention also more simplifies with respect to previous patent technology; The present invention can take disposable reinforced; The method of treating different things alike; And WO0100623 and US2004054189 report all require slowly to add acid binding agent, and to reduce the process of system blackening as far as possible, previous reported method has been simplified control process greatly.
Sharpest edges of the present invention are to the requirement of raw material 2-chloro-5-5-chloromethyl thiazole purity drop: the preparation technology of highly purified compd A is loaded down with trivial details, and is costly, and the inventive method is simplified technical process greatly and shortened the operational cycle, and reduces product cost.
Solvent acetone, acetonitrile price that reaction is used also are lower than methylcarbonate; The consumption of salt of wormwood also greatly reduces, and more seldom is that the yield of final thiophene worm piperazine product has reached 84%, purity 98%; Than aforementioned patent bigger lifting has been arranged, greatly reduced the generation of the three wastes simultaneously.
Embodiment
Below in conjunction with embodiment, the present invention is done to describe further.
The raw materials used manufacturing enterprise of following embodiment is following:
Intermediate A: the manufacturing enterprise of 2-chloro-5-5-chloromethyl thiazole is Shandong, Zhangjiagang this chemical industry ltd, and the purity of 2-chloro-5-5-chloromethyl thiazole is 95%.
Intermediate B: 3-methyl-4-nitro-imine base tetrahydrochysene-1,3, the manufacturing enterprise of 5-oxadiazine is chemical plant, eastern suburb, Liyang,
The manufacturing enterprise of acetonitrile, acetone, methylene dichloride, toluene is chemical plant, western Gansu Province,
The manufacturing enterprise of potassiumiodide, salt of wormwood is recovery chemical plant (ltd), Tianjin.
Embodiment 1
Get 18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3,5-oxadiazine and 16.8g2-chloro-5-5-chloromethyl thiazole are dissolved in the 180g acetone; Add the 0.4g potassiumiodide, 11g salt of wormwood, stirring at normal temperature 8h; The TLC detection reaction is complete, and this moment, system kept yellow outstanding turbid attitude always.40-50 ℃ of pressure reducing and steaming solvent acetone adds the 400g methylene dichloride and embathes in the residuum, filter and remove inorganic salt, collects filtrating; Organic phase is the deep yellow clear solution, and temperature 30-40 ℃ of evaporate to dryness methylene dichloride gets thick product, and thick product by heating to boiling is with 130g toluene recrystallization, backflow 0.5h; Be cooled to crystallizing at room temperature, suction filtration obtains beige thiophene worm piperazine 24.5g; Amount to yield 84%, purity 98%, mother liquor presents tawny.
Embodiment 2
Get 18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3,5-oxadiazine and 16.8g2-chloro-5-5-chloromethyl thiazole are dissolved in the 180g acetonitrile; Add the 0.4g potassiumiodide, 11g salt of wormwood, refluxing and stirring 12h; The TLC detection reaction is complete, and this moment, system kept deep yellow to hang turbid attitude always.60-70 ℃ of following pressure reducing and steaming acetonitrile that desolvates adds the 400g methylene dichloride and embathes in the residuum, temperature 30-40 ℃ of evaporate to dryness methylene dichloride gets thick product; Thick product by heating to boiling is with 130g toluene recrystallization, and backflow 0.5h is cooled to room temperature; Suction filtration; Obtain khaki color thiophene worm piperazine 23.2g, amount to yield 78%, purity 96%.
Embodiment 3
According to 2006Mu00715,18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3; The 5-oxadiazine, 27.6g salt of wormwood is dissolved among the 100mLDMF, dropwise adds 16.8g2-chloro-5-5-chloromethyl thiazole; Controlled temperature is in 60-65 ℃, stirring reaction 4h, the thorough blackening of reaction system.This system alkalescence is stronger, and a large amount of compound 2-chloro-5-5-chloromethyl thiazoles are at the reaction process mesometamorphism, and thiophene worm piperazine color is very dark, and yield is very low.
Embodiment 4
According to US2004054189,18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3; The 5-oxadiazine, 16.8g2-chloro-5-5-chloromethyl thiazole is dissolved in the 40g methylcarbonate, with mixture heating up to 65 ℃; Slowly add and contain the 35g methylcarbonate, 0.4g TMAH, the mixture of 24.2g salt of wormwood; TLC detects 2-chloro-5-5-chloromethyl thiazole and exhausts the terminal point for reaction, and this moment, system presented Vandyke brown.Cooling adds water 60g, and being adjusted to system with concentrated hydrochloric acid is neutrality, leaves standstill branch and manages out organic phase, concentrate till the about 60g of organic phase to total mass, and crystallisation by cooling, suction filtration obtains product and is dark-brown, yield 72%, purity 93%.System alkalescence is stronger, and thiophene worm piperazine color is darker, and yield purity is all on the low side.
Embodiment 5
18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3, the 5-oxadiazine; 16.8g2-chloro-5-5-chloromethyl thiazole is dissolved in the 180g acetone, adds the 0.4g TMAH, 11g salt of wormwood; Refluxing and stirring 8h, TLC detect does not almost have thiophene worm piperazine to generate, but system is obviously turned black.Present embodiment does not have thiophene worm piperazine to generate.
Embodiment 6
18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3, the 5-oxadiazine; 16.8g2-chloro-5-5-chloromethyl thiazole is dissolved in the 180g acetone, adds the 0.5g Tetrabutyl amonium bromide, 11g salt of wormwood; Refluxing and stirring 8h, TLC detect does not almost have thiophene worm piperazine to generate, but system obviously blackening.Present embodiment does not have thiophene worm piperazine to generate.
Embodiment 7
18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3, the 5-oxadiazine, 16.8g2-chloro-5-5-chloromethyl thiazole is dissolved in the 180g acetone, adds 11g salt of wormwood, and refluxing and stirring 12h, TLC detect does not almost have thiophene worm piperazine to generate, and it is faint yellow that system keeps always.Present embodiment does not have thiophene worm piperazine to generate.
Claims (3)
1. the preparation method of thiophene worm piperazine is characterized in that concrete operations are following:
Get 3-methyl-4-nitro-imine base tetrahydrochysene-1,3,5-oxadiazine and 2-chloro-5-5-chloromethyl thiazole are dissolved in the organic solvent of aprotic, polar; Add catalyzer potassiumiodide and acid binding agent salt of wormwood; Stirring at normal temperature 8h, the TLC detection reaction is complete, and reaction system keeps yellow outstanding turbid attitude always; Boil off organic solvent, be cooled to room temperature, add methylene dichloride in the residuum and embathe, filter and remove inorganic salt; Intercepting organic phase, organic phase are the deep yellow clear solution, room temperature evaporate to dryness methylene dichloride, and thick product is with the toluene recrystallization; Obtain beige thiophene worm piperazine, amount to yield 84%, purity 98%;
The quality of said catalyzer potassiumiodide is the 1-5% of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said acid binding agent salt of wormwood is 0.6-1 a times of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said organic solvent is 5-20 a times of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said methylene dichloride is 10-30 a times of 2-chloro-5-5-chloromethyl thiazole quality,
The quality of said toluene is 5-20 a times of 2-chloro-5-5-chloromethyl thiazole quality.
2. according to the preparation method of the said thiophene worm of claim 1 piperazine, it is characterized in that: the organic solvent of said aprotic, polar is acetone or acetonitrile.
3. according to the preparation method of claim 1 and 2 said thiophene worm piperazines, it is characterized in that: get 18.5g3-methyl-4-nitro-imine base tetrahydrochysene-1,3; 5-oxadiazine and 16.8g2-chloro-5-5-chloromethyl thiazole are dissolved in 180g acetone or the acetonitrile; Add the 0.4g potassiumiodide, 11g salt of wormwood, stirring at normal temperature 8h; The TLC detection reaction is complete, and this moment, reaction system kept yellow outstanding turbid attitude always; 20～55 ℃ of temperature, time 8～12h is cooled to room temperature, and temperature 40-70 ℃ boils off solvent acetone or acetonitrile; Add the 400g methylene dichloride in the residuum and embathe, filter and remove inorganic salt, filtrating is organic phase, and organic phase is the deep yellow clear solution; 35～40 ℃ of evaporate to dryness methylene dichloride of temperature get thick product, and thick product by heating to boiling is cooled to room temperature with 130g toluene recrystallization; Obtain beige thiophene worm piperazine, amount to yield 84%, purity 98%.
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Cited By (12)
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| CN103880832A (en) * | 2014-04-04 | 2014-06-25 | 连云港市金囤农化有限公司 | Preparation method of thiamethoxam |
| CN104016941A (en) * | 2014-03-17 | 2014-09-03 | 江苏辉腾生物医药科技有限公司 | Preparation method of 2-chlorine-5-chloromethylthiazole |
| GB2514927A (en) * | 2014-05-28 | 2014-12-10 | Rotam Agrochem Int Co Ltd | Thiamethoxam and uses thereof |
| CN106188032A (en) * | 2016-07-15 | 2016-12-07 | 南通天泽化工有限公司 | A kind of preparation method of Diacloden |
| CN106496215A (en) * | 2016-11-08 | 2017-03-15 | 邯郸市瑞田农药有限公司 | The environmental protection synthetic method in high yield of Diacloden |
| CN107400123A (en) * | 2017-08-28 | 2017-11-28 | 江苏绿叶农化有限公司 | A kind of production method of Diacloden |
| CN107698578A (en) * | 2017-10-31 | 2018-02-16 | 江苏绿叶农化有限公司 | A kind of preparation method of Diacloden |
| CN108822098A (en) * | 2018-06-29 | 2018-11-16 | 湖北犇星农化有限责任公司 | A kind of preparation method of Diacloden |
| GB2564284A (en) * | 2014-05-28 | 2019-01-09 | Rotam Agrochem Int Co Ltd | Thiamethoxam and uses thereof |
| EP3480196A1 (en) | 2017-11-02 | 2019-05-08 | Jiangsu Rotam Chemistry Co., Ltd | Process for the preparation of thiamethoxam |
| TWI662032B (en) * | 2014-05-28 | 2019-06-11 | 香港商龍燈農業化工國際有限公司 | Method of producing thiamethoxam |
| CN115286624A (en) * | 2022-08-04 | 2022-11-04 | 内蒙古犇星化学有限公司 | Preparation method of thiamethoxam |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104016941A (en) * | 2014-03-17 | 2014-09-03 | 江苏辉腾生物医药科技有限公司 | Preparation method of 2-chlorine-5-chloromethylthiazole |
| CN103880832A (en) * | 2014-04-04 | 2014-06-25 | 连云港市金囤农化有限公司 | Preparation method of thiamethoxam |
| GB2564284A (en) * | 2014-05-28 | 2019-01-09 | Rotam Agrochem Int Co Ltd | Thiamethoxam and uses thereof |
| GB2514927A (en) * | 2014-05-28 | 2014-12-10 | Rotam Agrochem Int Co Ltd | Thiamethoxam and uses thereof |
| CN105175407A (en) * | 2014-05-28 | 2015-12-23 | 龙灯农业化工国际有限公司 | Thiamethoxam and uses thereof |
| TWI687417B (en) * | 2014-05-28 | 2020-03-11 | 香港商龍燈農業化工國際有限公司 | Thiamethoxam and uses thereof |
| CN105175407B (en) * | 2014-05-28 | 2020-02-07 | 龙灯农业化工国际有限公司 | Thiamethoxam and application thereof |
| TWI662032B (en) * | 2014-05-28 | 2019-06-11 | 香港商龍燈農業化工國際有限公司 | Method of producing thiamethoxam |
| GB2514927B (en) * | 2014-05-28 | 2019-04-17 | Rotam Agrochem Int Co Ltd | Thiamethoxam and uses thereof |
| CN106188032A (en) * | 2016-07-15 | 2016-12-07 | 南通天泽化工有限公司 | A kind of preparation method of Diacloden |
| CN106496215A (en) * | 2016-11-08 | 2017-03-15 | 邯郸市瑞田农药有限公司 | The environmental protection synthetic method in high yield of Diacloden |
| CN106496215B (en) * | 2016-11-08 | 2020-04-07 | 邯郸市瑞田农药有限公司 | High-yield green environment-friendly synthetic method of thiamethoxam |
| CN107400123A (en) * | 2017-08-28 | 2017-11-28 | 江苏绿叶农化有限公司 | A kind of production method of Diacloden |
| CN107698578A (en) * | 2017-10-31 | 2018-02-16 | 江苏绿叶农化有限公司 | A kind of preparation method of Diacloden |
| EP3480196A1 (en) | 2017-11-02 | 2019-05-08 | Jiangsu Rotam Chemistry Co., Ltd | Process for the preparation of thiamethoxam |
| CN111315743A (en) * | 2017-11-02 | 2020-06-19 | 江苏龙灯化学有限公司 | Method for preparing thiamethoxam |
| CN108822098A (en) * | 2018-06-29 | 2018-11-16 | 湖北犇星农化有限责任公司 | A kind of preparation method of Diacloden |
| CN115286624A (en) * | 2022-08-04 | 2022-11-04 | 内蒙古犇星化学有限公司 | Preparation method of thiamethoxam |
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Application publication date: 20120314 |