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The preparation method of 2-chloro-5-chloromethylthiazole

A chloromethylthiazole and chlorine technology, applied in organic chemistry and other directions, can solve the problems of large influence on reaction yield, low product purity, harsh reaction conditions, etc., and achieve good mass transfer and heat transfer effect and process controllability. Strong, mild reaction conditions

Active Publication Date: 2020-01-17
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The above-mentioned method (1) has problems such as a large amount of chlorine gas required and many side reactions.
Both purity and yield are low
In the second method, the cis-trans ratio of the raw material 1-isothiocyanato-3-chloro-1-propene has a great influence on the reaction yield, and the post-treatment of the catalyst is more complicated, which is not suitable for industrial production
The third method has mild reaction conditions and convenient operation, and is more suitable for industrial production, but it has problems such as long reaction time and low product purity.
Both methods (4) and (5) have problems such as low reaction yield, harsh diazotization reaction conditions, large amount of hydrochloric acid and unrecyclable, etc., and are not suitable for large-scale industrial production.
Compared with the first five methods, the (6) method solves the problem of low yield and purity, but it has problems such as longer reaction time, more complicated operation, and strict temperature requirements; at the same time, iodine is used as a catalyst, and N - Chlorinated succinimide is used as a chlorination reagent, and the production cost is also relatively high
The (7) method has problems such as long reaction time, large amount of washing wastewater and cannot be recycled, and is not suitable for green and clean industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 0.8g composite initiator (a mixture of benzoyl peroxide and N,N-dimethylaniline, the mass ratio of the two is 1:1) was stirred and dissolved in 1-isothiocyanato-2-chloro-2-propene 26.6g (0.2moL), a mixed solution was obtained. Keep the temperature in the microreactor at 10°C, pump the mixed solution into the first plate of the microreactor at a speed of 1.3g / min through a plunger pump, and simultaneously flow 14.2g (0.2moL) of chlorine gas at a rate of 0.7 The speed of g / min is passed into the second plate of the microreactor, and the materials are mixed on the mixing plate, and the material is fed and discharged continuously, and the reaction liquid is collected, and then 30.2g of 2-chloro-5-chloromethylthiazole is obtained by catching hydrogen chloride and distillation. , content 97.5%, yield 87.6% (1-isothiocyanato-2-chloro-2-propene).

Embodiment 2

[0042] 0.8g composite initiator (a mixture of benzoyl peroxide and N,N-dimethylaniline, the mass ratio of the two is 1:1) was stirred and dissolved in 1-isothiocyanato-2-chloro-2-propene 26.6g (0.2moL), a mixed solution was obtained. Keep the temperature in the microreactor at 20°C, pump the mixed solution into the first plate of the microreactor at a speed of 1.3g / min through a plunger pump, and simultaneously flow 14.2g (0.2moL) of chlorine gas at a rate of 0.7 The speed of g / min is passed into the second plate of the microreactor, and the materials are mixed on the mixing plate, and the material is continuously fed and discharged, and the reaction solution is collected, and then 30.8g of 2-chloro-5-chloromethylthiazole is obtained by catching hydrogen chloride and distillation. , content 99.5%, yield 91.2% (1-isothiocyanato-2-chloro-2-propene).

Embodiment 3

[0044] 0.8g composite initiator (a mixture of benzoyl peroxide and N,N-dimethylaniline, the mass ratio of the two is 1:1) was stirred and dissolved in 1-isothiocyanato-2-chloro-2-propene 26.6g (0.2moL), a mixed solution was obtained. Keep the temperature in the microreactor at 50°C, pump the mixed solution into the first plate of the microreactor at a speed of 1.3g / min through a plunger pump, and simultaneously flow 14.2g (0.2moL) of chlorine gas at a rate of 0.7 The speed of g / min is passed into the second plate of the microreactor, and the materials are mixed on the mixing plate, and the material is continuously fed and discharged, and the reaction solution is collected, and then 30.3g of 2-chloro-5-chloromethylthiazole is obtained by catching hydrogen chloride and distillation. , content 94%, yield 84.8% (1-isothiocyanato-2-chloro-2-propene).

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PUM

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Abstract

The invention discloses a method for preparing 2-chloro-5-chloromethylthiazole. The method comprises the following steps: in a micro-reactor and under a solvent-free condition, a chlorination reactionof chlorine and 1-isothiocyano-2-chloro-2-propylene is performed under the action of a composite initiator, and 2-chloro-5-chloromethylthiazole is prepared and obtained. The method has the advantagesof being free of solvent, low in cost, gentle in reaction condition, high in reaction speed, relatively small in the amount of three wastes, simple in process, relatively high in target product yield, relatively high in purity, and the like.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates, in particular to a preparation method of 2-chloro-5-chloromethylthiazole. Background technique [0002] 2-Chloro-5-chloromethylthiazole (abbreviated as CCMT) is the key intermediate of thiamethoxam and clothianidin, the second-generation nicotinic insecticide thiazole pesticides, and can also be combined with heterocyclic N-H Condensation to prepare a series of insecticides and miticides, and used in the synthesis of 5-hydroxymethylthiazole, an intermediate of anti-AIDS drug ritonavir. [0003] Thiazole pesticides imitate the action mechanism of tobacco alkaloids. By acting on nicotinic acetylcholine receptors, they have no cross-resistance to conventional pyrethroids, organophosphates, and carbamate insecticides, and they also have rapid degradation. , Short half-life in the soil, the advantages of biological safety, can widely control piercing-sucking pests and v...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/32
CPCC07D277/32
Inventor 程超杜升华刘卫东刘源王艳丽兰世林
Owner HUNAN CHEM RES INST
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