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Method for synthesizing 5-amino-1,2,3-thiadiazole

A synthetic method, thiadiazole technology, applied in the field of 5-amino-1,2,3-thiadiazole synthesis, can solve the problems of high requirements for protective equipment, difficult operation, heavy exhaust gas pollution, etc., and achieve catalytic Remarkable effect, simple equipment requirements, improved conversion rate and selectivity

Inactive Publication Date: 2018-12-21
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the traditional synthesis, diazomethane, a highly toxic and explosive raw material, is used in the reaction, which is difficult to operate, requires high protection equipment, and uses volatile ether as a solvent, and generates a large amount of waste water containing acid and diazonium salts. The three wastes are serious.
However, formaldehyde and sodium cyanide are condensed to generate methyliminoacetonitrile, and sulfuric acid is used to catalyze alcoholysis to obtain aminoacetonitrile sulfate, and finally the product is obtained through diazotization and hydrogen sulfide cyclization, and the highly toxic raw material potassium cyanide or cyanide is also used. Sodium, one-step reaction with hydrogen sulfide to produce products has a low yield, and hydrogen sulfide gas is generated during the reaction, causing serious waste gas pollution

Method used

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  • Method for synthesizing 5-amino-1,2,3-thiadiazole

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Embodiment 1

[0020] 1. A synthetic method for intermediate 5-amino-1,2,3-thiadiazole, characterized in that the method comprises the following steps:

[0021] Step 1. Install a mechanical stirrer on a 50ml three-necked flask poured into 30ml of anhydrous chloroform, add 7.5g of thionyl chloride and 5g of [HOOC-PECH-MIM] Cl catalyst, control the temperature in an ice-water bath at 30°C, and slowly add 12g 2-Chloroethyl hydrazonocarboxylate methyl, rapid stirring reaction 24h under ice-water bath;

[0022] Step 2, under the condition of ice-water bath cooling, slowly add 10% sodium hydroxide solution dropwise to make the reaction solution PH=10;

[0023] Step 3. The reaction solution was distilled with steam, and the lower chloroform layer was separated. The aqueous layer was extracted three times with chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was evaporated to dryness. The residue was distilled under reduced pressure to obtain the ...

Embodiment 2

[0035] Step 1. Install mechanical stirring on a 50ml three-necked flask poured into 30ml of anhydrous chloroform, add 6.5g of thionyl chloride and 5g of [HOOC-PECH-MIM] Cl catalyst, control the temperature in an ice-water bath at 30°C, and slowly add 12g 2-Chloroethyl hydrazinocarboxylate methyl ester, rapid stirring reaction 24h under ice-water bath;

Embodiment 3

[0037] Step 1. Install a mechanical stirrer on a 50ml three-necked flask poured into 30ml of anhydrous chloroform, add 5.5g of thionyl chloride and 5g of [HOOC-PECH-MIM] Cl catalyst, control the temperature in an ice-water bath at 30°C, and slowly add 12g 2-Chloroethyl hydrazinocarboxylate methyl ester, rapid stirring reaction 24h under ice-water bath;

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Abstract

The invention discloses a method for synthesizing an intermediate 5-amino-1,2,3-thiadiazole. The intermediate 5-amino-1,2,3-thiadiazole is prepared from anhydrous chloroform, thionyl chloride, 2-chloroethyl hydrazono methyl formate, boron trifluoride diethyl ether, dichloroethane, epichlorohydrin and N-methylimidazole; according to the synthesis process, the 2-chloroethyl hydrazono methyl formateand the thionyl chloride are subjected to cyclized substitution reaction under the action of a catalyst [HOOC-PECH-MIM]Cl to obtain the 5-amino-1,2,3-thiadiazole; the reaction operation is simple, and the main operation process includes stirring at room temperature, steam distillation and crystallization, so that the equipment requirements are simple, special equipment requirements are avoided, the intermediate product can be subjected to the next step without purification, the synthesis process is smooth, and the reaction yield is high.

Description

technical field [0001] The invention relates to a synthesis method of 5-amino-1,2,3-thiadiazole, which belongs to the field of chemical synthesis. Background technique [0002] 5-Amino-1,2,3-thiadiazole (5-Amino-1,2,3-thiadiazole) CAS: 4100-41-85 is an important medicine and pesticide center. It is light yellow to amber needle-like or flaky crystals, soluble in methylene chloride and carbon tetrachloride, soluble in ethanol, acetone and other organic solvents, insoluble in water. The traditional synthesis uses diazomethane, a highly toxic and explosive raw material, which is difficult to operate and requires high protection equipment, and uses volatile ether as a solvent, and generates a large amount of waste water containing acid and diazonium salts, which is a serious waste. Formaldehyde and sodium cyanide are used to condense formaldehyde and sodium cyanide to generate methyliminoacetonitrile, and sulfuric acid is used to catalyze alcoholysis to obtain aminoacetonitrile ...

Claims

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Application Information

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IPC IPC(8): C07D285/06B01J31/06
CPCC07D285/06B01J31/0284B01J31/06
Inventor 张永伟张刚高光珍
Owner XUZHOU NORMAL UNIVERSITY