5-amino-1,2,4-thiadiazole compound and preparation method thereof

A technology for thiadiazoles and compounds, which is applied in the field of organic chemical synthesis, can solve the problems of unsuitable industrial production, complicated preparation methods, increased cost and the like, and achieves the effects of avoiding corrosiveness and toxicity, simple reaction process and reducing pollution.

Inactive Publication Date: 2012-05-30
临沂明辉再生资源有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the preparation method of 1,2,4-thiadiazole compounds is relatively complicated, and it is necessary to design a synthetic route based on different types of starting materials based on the molecular structure of the target product
However, a large amount of bromine needs to be used in the existing synthetic methods, and bromine has extremely strong toxicity and corrosiveness, and is volatile, causing waste of raw materials, cost increase and environmental pollution, so it is not suitable for industrial production

Method used

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  • 5-amino-1,2,4-thiadiazole compound and preparation method thereof
  • 5-amino-1,2,4-thiadiazole compound and preparation method thereof
  • 5-amino-1,2,4-thiadiazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1: Synthesis of 3-(2-pyridyl)-5-amino-1,2,4-thiadiazole

[0013] Weigh 52g (0.5mol) of 2-cyanopyridine in a 250mL round-bottomed flask, add 200mL of methanol to dissolve it, add 5.6g (0.052mol) of methanol solution of sodium methoxide with a mass percentage of 50%, and magnetically stir the reaction at room temperature 3h. After adding 27.5 g (0.515 mol) of ammonium chloride into the above system, the reaction was continued at room temperature for 48 h. The end point of the reaction was tracked by TLC. After the reaction was completed, the solvent was evaporated to dryness, and the remaining solid was washed with ether, filtered, and repeated three times. The filter cake was recrystallized with hot water (about 60 ° C) and ethanol in turn to obtain white needle-shaped crystals of 2-formamidinyl Pyridine hydrochloride 66.9g, yield 85%.

[0014] Weigh 59.0 g (0.375 mol) of 2-formamidinopyridine hydrochloride and place it in a 500 mL round-bottomed flask, add 250...

Embodiment 2

[0020] Example 2: Synthesis of 3-(3-pyridyl)-5-amino-1,2,4-thiadiazole

[0021] Weigh 52g (0.5mol) of 3-cyanopyridine in a 250mL round bottom flask, add 200mL of methanol to dissolve it, add 5.6g (0.052mol) of methanol solution of sodium methoxide with a mass percentage of 50%, and magnetically stir the reaction at room temperature 4h. After adding 27.5 g (0.515 mol) of ammonium chloride into the above system, the reaction was continued at room temperature for 48 h. The end point of the reaction was tracked by TLC. After the reaction was completed, the solvent was evaporated to dryness. The remaining solid was washed with ether, filtered, and repeated three times. Pyridine hydrochloride 60.5g, yield 76.8%.

[0022] Weigh 59.0 g (0.375 mol) of 3-formamidinopyridine hydrochloride and place it in a 500 mL round bottom flask, add 250 mL of water to dissolve it, and add 280 g (0.376 mol) of 10% sodium hypochlorite aqueous solution dropwise under ice-water bath conditions . Afte...

Embodiment 3

[0028] Example 3: Synthesis of 3-(4-pyridyl)-5-amino-1,2,4-thiadiazole

[0029] Weigh 52g (0.5mol) of 4-cyanopyridine in a 250mL round bottom flask, add 200mL of methanol to dissolve it, add 5.6g (0.052mol) of methanol solution of sodium methoxide with a mass percentage of 50%, and magnetically stir the reaction at room temperature 4h. After adding 27.5 g (0.515 mol) of ammonium chloride into the above system, the reaction was continued at room temperature for 48 h. The end point of the reaction was tracked by TLC. After the reaction was completed, the solvent was evaporated to dryness, and the remaining solid was washed with ether, filtered, and repeated three times. The filter cake was recrystallized with hot water (about 60 ° C) and ethanol in turn to obtain white needle-shaped crystals of 4-formamidino Pyridine hydrochloride 72.4g, yield 92%.

[0030] Weigh 59.0 g (0.375 mol) of 4-formamidinopyridine hydrochloride and place it in a 500 mL round bottom flask, add 250 mL o...

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Abstract

The invention relates to a 5-amino-1,2,4-thiadiazole compound and a preparation method thereof. The preparation method comprises the following steps of: dissolving a cyan compound into methanol, adding a methanol solution of sodium methoxide, stirring at 20-50 DEG C for reacting for 3-4 hours, adding ammonium chloride for reacting at room temperature for 48 hours, evaporating a reaction solvent, washing by diethyl ether, then recrystallizing sequentially by water and alcohol, filtering, drying and obtaining an intermediate amidine compound; dissolving the intermediate amidine compound into water, slowly and dropwise adding a sodium hypochlorite water solution under ice water bath, heating to room temperature and stirring for reacting for 4-5 hours, filtering, washing by water, and drying;and dissolving a filter cake into methanol, slowly and dropwise adding the methanol solution of potassium rhodanide under the ice water bath, reacting at room temperature for 12 hours, filtering, rotatably evaporating the obtained filtrate, recrystallizing by methanol and water, filtering, and drying. The synthesized 5-amino-1,2,4-thiadiazole compound has the structure in a general formula (I). The invention has simple reaction process, mild conditions and less environmental pollution.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically relates to 5-amino-1,2,4-thiadiazole compounds and a preparation method thereof. Background technique [0002] Nitrogen-containing heterocyclic compounds play an extremely important role in today's pesticide and pharmaceutical research, for example, thiadiazoles are one of them. Because the "carbon sulfur nitrogen" structure in the thiadiazole ring has biological activities such as insecticide, antibacterial, and plant growth regulation, the synthesis and properties of this type of compound have attracted more and more attention. Early research hotspots mainly focused on the most common and common 1,3,4-thiadiazole compounds (Nakhmanovich A.S., Glotova T.E., Komarova T.E., et al., Chemistry of Heterocyclic Compounds, 1990, 26, 1186 ; Rutavichyus A., Valyulene S., Kuodis Z., Chemistry of Heterocyclic Compounds, 1997, 33, 118; Gadad A.K., Mahajanshetti C.S., Nimbalkar S.,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D285/08
Inventor 严欣宁张慧东李丹董明东杜存锐
Owner 临沂明辉再生资源有限公司
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