105827-91-6Relevant articles and documents
Synthesis, characterization and crystal structure of n-(3-((2-chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide
He, Jian-Ling,Cheng, Wei-Hua
, p. 2383 - 2385 (2015)
N-(3-[(2-chlorothiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide (I), i.e., thiamethoxam, it is a broad-spectrum insecticide that effectively controls insects, being a second generation neonicotinoid compound belonging to the chemical subclass the thianicotinyls. It was prepared from 5-(chloromethyl)-2-(phenylthio)thiazole (1) via chlorination by Cl2/HCl system and then condensation by K2CO3/CsI. The product was characterized by NMR and LC-MS. The crystal structure of compound I was investigated using X-ray diffraction and SHELXTL-97 software. The result indicated that compound I crystallized in the monoclinic system, space group P 21/n with a = 6.488(13), b = 28.786 (6), c = 6.804(14) ?, V=1225.1 (5) ?3; Z4.
Synthesis process of 2-chloro-5-chloromethylthiazole
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Paragraph 0032-0039, (2021/07/17)
The invention discloses a synthesis process of 2-chloro-5-chloromethylthiazole, and relates to the technical field of synthesis of 2-chloro-5-chloromethylthiazole. The method comprises the following steps: adding excessive sodium thiocyanate, water and a catalyst C2 into a reactor, slowly adding 2, 3-dichloropropene under the conditions of ultrasonic shearing and stirring, stopping ultrasonic treatment after the addition is completed, keeping stirring, slowly heating the mixed solution to reflux, and keeping the temperature until the reaction is complete; stopping stirring after the reaction is completed, carrying out primary standing layering, separating and transferring a primary organic layer into a distillation kettle after complete layering, stirring the residual solution, carrying out ultrasonic uniform mixing, carrying out secondary standing layering, separating and transferring a secondary organic layer into the distillation kettle after complete layering, and carrying out reduced pressure distillation to obtain an intermediate product; and adding the intermediate product and trichloromethane into a reactor, stirring at normal temperature, slowly dropwise adding sufficient sulfuryl chloride, and stirring at 45-55 DEG C until the reaction is complete after dropwise adding. The method is simple in process, low in raw material cost and high in product yield.
Synthesis method of 2-chloro-5-chloromethylthiazole by photocatalytic chlorination
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Paragraph 0023-0032, (2021/04/17)
The invention relates to the technical field of synthesis of 2-chloro-5-chloromethylthiazole, and provides a synthesis method of 2-chloro-5-chloromethylthiazole by photocatalytic chlorination, which comprises the following steps: S1. adding 2-chloropropenyl thioisocyanate, sulfonyl chloride and acetonitrile into a tower reactor, and stirring to dissolve; S2, adding a catalyst, irradiating with ultraviolet light, and starting chlorination reaction; S3, carrying out reduced pressure distillation to remove the solvent acetonitrile; S4, dissolving distilled residues in dichloromethane, respectively washing with a NaHCO3 solution and water to be neutral, and carrying out reduced pressure distillation to obtain a 2-chloro-5-chloro methylthiazole product. Through the technical scheme, the problems of poor product quality and low yield in the prior art are solved.
Continuous production process of 2-chloro-5-chloromethylthiazole
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Paragraph 0049-0072, (2021/10/27)
The invention provides a continuous production process of 2-chloro-5-chloromethylthiazole, which comprises the following steps of providing an organic solvent, and mixing a raw material 2-chloro-3-isothiocyano-1-propylene into the organic solvent to form a mixed solution, providing a continuous chlorination device, introducing chlorine into the device, and carrying out chlorination reaction, providing a rectification device, and sequentially carrying out solvent distillation removal, light component distillation removal and heavy component removal rectification in a vacuum state to obtain a 2-chloro-5-chloromethylthiazole product. The chlorination reaction is carried out in a continuous feeding and continuous overflowing manner; and the rectification device adopts the operation conditions of continuous feeding and continuous vacuum rectification. According to the process, the content of 2-chloro-5-chloromethylthiazole is increased to 99% or above, the content of by-products is reduced by 0.5% or below, the yield is increased to 91% or above, continuous production is safe and controllable, the generation amount of by-products and wastes is small, the product quality is stable, and green, environment-friendly and safe industrial production is achieved.
Tower reactor preparation 2 chloro -5 chloro - methylthiazole
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Paragraph 0021; 0024-0026; 0029-0031; 0034-0035; 0038; ..., (2021/11/10)
The invention relates to the technical field 2 chlorine -5 chlorine - methylthiazole preparation, in particular to a tower reactor for preparing 2 chloro -5 chloro - methylthiazole, which comprises the following steps: S1. The sodium thiocyanate and the catalyst tetrabutylammonium bromide are added into the tower reactor, and then are metered into 2, 3 - dichloropropene and toluene respectively, stirred and heated to reflux. S2, followed by addition of tetrabutylammonium bromide, and isomerization reaction was performed after the temperature increase, and after completion of the reaction, negative pressure distillation was performed to obtain 2 - chloroallyl isothiocyanate. To the method, pollution to the environment can be reduced, hydrogen chloride gas generated in the reaction process can be reused, and the problem that the color of the product 2 chlorine -5 chlorine - methyl thiazole is too deep can be solved.
Clean and environment-friendly production process of 2-chloro-5-chloromethylthiazole
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Paragraph 0016; 0022-0024, (2020/10/30)
The invention relates to a clean and environment-friendly production process of 2-chloro-5-chloromethylthiazole, which comprises the following steps: dissolving sodium thiocyanate in water, dropwiselyadding 2, 3-dichloropropene, carrying out heat preservation reaction after the dropwisely adding is completed, washing the obtained material with water, layering, and distilling to obtain an intermediate product 2-chloropropenyl isothiocyanate; dissolving the intermediate product in dichloroethane, dropwise adding sulfonyl chloride for the first time at the temperature of 30-60 DEG C, carrying out heat preservation reaction after dropwise adding is finished, degassing, desolventizing and cooling the obtained material, dropwise adding sulfonyl chloride for the second time, carrying out heat preservation reaction after dropwise adding for the second time, adding a stabilizer into the obtained material, and distilling to obtain 2-chloro-5-chloromethylthiazole. According to the invention, a pure byproduct sodium chloride is obtained, and the problem of high ammonia-nitrogen wastewater is solved. Due to the fact that the sulfonyl chloride is appropriate in use amount and is added in two times, by-products of sulfur dioxide and hydrogen chloride gas are reduced, the problem of environmental pollution is solved, and the production process is mild in reaction condition, small in toxicity,high in yield and purity and environmentally friendly.
Continuous synthesis method of 2-chloro-5-chloromethylthiazole
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Paragraph 0029-0044, (2020/11/01)
The invention discloses a continuous synthesis method of 2-chloro-5-chloromethylthiazole. The continuous synthesis method comprises the following steps: step 1, adding a diluting solvent into a chlorination reaction device; step 2, gradually spraying a 2-chloro-3-isothiocyano-1-propylene solution into the chlorination reaction device, meanwhile, gradually introducing chlorine, carrying out a reaction, controlling the reaction temperature to range from 18 DEG C to 40 DEG C, then carrying out heat preservation till the reaction is completed, and thus obtaining a reaction material; and step 3, desolventizing, removing light components, and rectifying to obtain the 2-chloro-5-chloromethylthiazole product. Continuous reaction is adopted in the invention, compared with an existing process, the product quality and the product yield are greatly improved by controlling the addition of chlorine; the mass content of the 2-chloro-5-chloromethylthiazole is increased from 98.5% to 99.0% or above inthe process; by-products are reduced from 1.0% to 0.2% or below, the chlorination reaction yield is greatly increased to 92% compared with 75% of the existing process, the quality of the continuous feeding reaction process is stable, the total concentration of materials participating in the reaction is low, the production process is safe and controllable, and thus the green, environment-friendly and safe industrial production process is achieved.
Thiamethoxam and uses thereof
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Paragraph 0081-0084, (2020/02/17)
A crystalline form of 3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl 1,3,5-oxadiazinan-yledene (nitro)amine (thiamethoxam) is provided. The crystalline form exhibits an X-ray powder diffraction pattern having characteristic peaks (expressed in degrees 2?? +/- 0.2?° ??) at one or more of the following positions: 6.09, 15.37, 17.83, 18.43, 20.86, 22.01, 26.95 and 27.84, and an Infrared (IR) spectrum having characteristic peaks at about 2933.62, 2161.78 and 1593.88 cm-1. A method of preparing the crystalline form comprises crystallizing 3-(2-chloro-1,3-thiazol-5-ylmethyl)-5-methyl-1,3,5-oxadiazinan -4-yledene (nitro)amine (thiamethoxam) from a solvent system comprising a solvent selected from an alcohol, a glycol, an ether, a ketone, an ester, an amide, a nitrile, an aliphatic or aromatic hydrocarbon, or mixtures thereof; and isolating the resulting crystals. The exemplified solvents are methanol, ethanol, 1-propanol, ethylene glycol, toluene and xylene.
Thiamethoxam production method and extractant
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Paragraph 0088-0090; 0093, (2020/05/01)
The invention provides a thiamethoxam production method and an extractant, belongs to the technical field of pesticides, particularly provides an extractant taking ethylene glycol salicylate as a complexing agent, and also provides a composite extractant. The extractant comprises a complexing agent and a diluent, and the complexing agent comprises the ethylene glycol salicylate and P204, wherein the extraction ratio of ethylene glycol salicylate to P204 is 1:1.5 to 1:2. The ethylene glycol salicylate used as the complexing agent and -N- of thiamethoxam have strong ion association to generate an ion extract with the same structure, so that the distribution ratio is increased; and when the extractant and the P204 are used for composite extraction, hydrogen bond association of the strong electron withdrawing group nitro -NO2 of thiamethoxam and -OH of P204 can be promoted, and when the extraction ratio of ethylene glycol salicylate to the P204 extractant is 1:(1.5-2), the distribution ratio can be synergistically increased, and the extraction rate is increased.
A synthetic method of 2-chloro-5-chloromethyl thiazole
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Paragraph 0016-0018, (2019/06/07)
A synthetic method of 2-chloro-5-chloromethyl thiazole is provided. The method includes adding 2,3-dichloropropene and sodium thiocyanate into an organic solvent, reacting the mixture, processing thereaction solution to obtain colorless liquid that is 2-chloroallyl isothiocyanate; then dissolving the 2-chloroallyl isothiocyanate into an organic solvent, adding hydrochloric acid and performing electrolysis to obtain the 2-chloro-5-chloromethyl thiazole. No chlorine is directly used in the synthetic process, while the 2-chloro-5-chloromethyl thiazole is synthesized through electrochemical chlorination, thus avoiding harm caused by chlorine, increasing the synthesis efficiency and saving the water resource and energy. In addition, the electrolytic reaction has high selectivity and the purityof the synthesized 2-chloro-5-chloromethyl thiazole is high. The method is suitable for synthesizing the 2-chloro-5-chloromethyl thiazole and further used for synthesizing thiamethoxam as an insecticide.
