Imidaclothiz synthesis method

A synthesis method and chlorothiline technology, applied in the direction of organic chemistry and the like, can solve the problems of decreased product content and yield, decreased product content, difficult removal of double-substituted by-products, etc., and achieve the effect of improving yield and content

Active Publication Date: 2017-10-10
NANTONG TENDENCI CHEM
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] At present, the following method is generally adopted to synthesize chlorothiline, 2-chloro-5-chloromethylthiazole and 2-nitroiminoimidazolidine, in the reaction solvent, under the action of a catalyst, an electrophilic substitution reaction occurs, and the hydrogen chloride produced Adopt acid-binding agent to neutralize and condense to obtain chlorothialine product; Reaction equation: During the condensation reaction, if there is an excess of 2-nitroimidazolidine, the excess imidazolidine will p

Method used

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Embodiment 1

[0016] The synthetic method of present embodiment chlorothialine, this synthetic method adopts nitroguanidine, ethylenediamine to react, and the intermediate of generation prepares chlorothialine with 2-chloro-5-chloromethylthiazole, concrete steps are as follows:

[0017] Add 125g of nitroguanidine and 50g of 70% sulfuric acid to a 500ml four-necked flask in sequence, add 32g of ethylenediamine dropwise, heat up to 80°C for reaction, and filter, wash and dry to obtain the intermediate imidazolidine after the reaction is completed.

[0018] Add 100mL of toluene, 132g of imidazolidine, 20g of potassium carbonate, and tetrabutylammonium bromide into a 1000ml four-neck flask, mix a little, add dropwise 200mL of toluene solution in which 2-chloro-5-chloromethylthiazole is dissolved, and heat at 45°C After reacting for 6 hours, the temperature was lowered, the layers were separated, and 247 g of a yellow solid was obtained by precipitation.

[0019] The content of chlorothialine in...

Embodiment 2

[0021] The synthetic method of present embodiment chlorothialine, this synthetic method adopts nitroguanidine, ethylenediamine to react, and the intermediate of generation prepares chlorothialine with 2-chloro-5-chloromethylthiazole, concrete steps are as follows:

[0022] Add 125g of nitroguanidine, 50g of 70% sulfuric acid in sequence in a 500ml four-neck flask, dropwise add 32g of ethylenediamine, raise the temperature to 90°C for reaction, and filter, wash and dry the intermediate product imidazolidine after the reaction is completed.

[0023] Add 100mL of toluene, 132g of imidazolidine, 20g of potassium carbonate, and tetrabutylammonium bromide into a 1000ml four-neck flask, mix a little, add dropwise 200mL of toluene solution in which 2-chloro-5-chloromethylthiazole is dissolved, and heat at 49°C After reacting for 8 hours, the temperature was lowered, the layers were separated, and 249 g of a yellow solid was obtained by precipitation.

[0024] The content of chlorothia...

Embodiment 3

[0026] The synthetic method of present embodiment chlorothialine, this synthetic method adopts nitroguanidine, ethylenediamine to react, and the intermediate of generation prepares chlorothialine with 2-chloro-5-chloromethylthiazole, concrete steps are as follows:

[0027] Add 125g of nitroguanidine and 50g of 70% sulfuric acid successively into a 500ml four-neck flask, dropwise add 32g of ethylenediamine, raise the temperature to 85°C for reaction, and filter, wash and dry to obtain the intermediate imidazolidine after the reaction is completed.

[0028] Add 100mL of toluene, 132g of imidazolidine, 20g of potassium carbonate, and tetrabutylammonium bromide into a 1000ml four-neck flask, mix a little, add dropwise 200mL of toluene solution dissolved in 2-chloro-5-chloromethylthiazole, and heat at 47°C After reacting for 7 hours, the temperature was lowered, the layers were separated, and 252 g of a yellow solid was obtained by precipitation.

[0029] In the present embodiment,...

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Abstract

The invention relates to an imidaclothiz synthesis method. The imidaclothiz synthesis method comprises steps as follows: (1), nitroguanidine with water content being 50% and sulfuric acid with mass concentration being 70% are added to a reaction kettle A, ethanediamine is dropwise added, the temperature is increased to 80-90 DEG C for a reaction, a product is filtered, washed and dried after the reaction, and an intermediate alkylimidazole is obtained; (2), toluene, alkylimidazole, potassium carbonate and tetrabutylammonium bromide are sequentially added to a reaction kettle B, a mixed solution is formed, a toluene solution with dissolved 2-chloro-5-chloromethylthiazole is dropwise added, a heating reaction is performed at the temperature of 45-49 DEG C for 6-8 h, finally, the solution is left to stand for layering, and yellow solid imidaclothiz is obtained through desolventizing. The imidaclothiz synthesis method has the advantages that side reactions are controlled by dropwise adding ethanediamine in an alkylimidazole generating process, meanwhile, the consumption ratio of the raw materials in the reactions is controlled strictly, so that the yield and the content of the imidaclothiz product can be greatly increased, the yield can be increased to 90% or higher, and the content of the imidaclothiz product can be increased to 95% or higher.

Description

technical field [0001] The invention belongs to the technical field of insecticide preparation, in particular to a synthesis method of chlorothialine. Background technique [0002] Chlorthialine is a systemic insecticide that acts on nicotinic acetylcholinesterase receptors, and has a blocking effect on the conduction of synaptic nerves in pests. Chlorothialine has the characteristics of broad spectrum, high efficiency, low toxicity, low residue, no resistance to pests, and is safe to humans, animals, plants and natural enemies. [0003] At present, the following method is generally adopted to synthesize chlorothiline, 2-chloro-5-chloromethylthiazole and 2-nitroiminoimidazolidine, in the reaction solvent, under the action of a catalyst, an electrophilic substitution reaction occurs, and the hydrogen chloride produced Adopt acid-binding agent to neutralize and condense to obtain chlorothialine product; Reaction equation: During the condensation reaction, if there is an exc...

Claims

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Application Information

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IPC IPC(8): C07D417/06
CPCC07D417/06
Inventor 张赟金标
Owner NANTONG TENDENCI CHEM
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