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Synthetic method of N-(6-chloro-3-pyridazinyl) acetamide

A synthetic method, pyridazine-based technology, applied in the field of synthesis of N-acetamide, can solve the problems of difficult synthesis, high market price, lack of literature and related patent reports, etc., and achieve simple post-processing, easy promotion, and easy control of the reaction Effect

Pending Publication Date: 2017-05-17
陕西友帮生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] N-(6-chloro-3-pyridazinyl)acetamide is an important organic intermediate widely used in the synthesis of medicines, pesticides, dyes and colorants, rubber accelerators and chemical reagents. This product has great value , its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 3-amino-6-chloropyridazine (1.30g, 10mmol), glacial acetic acid (0.90g, 15mmol) and 20mL (15.8g) ethanol in a 100ml single-necked round bottom flask, start the magnetic stirrer, and the The mixture was stirred and reacted at 90°C for 10 hours. TLC and GC detection confirmed that the reaction of raw material 3-amino-6-chloropyridazine was complete. The reaction solution was suction filtered, and the filter cake was recrystallized from a mixture of ethyl acetate and n-hexane to obtain the pure product N-(6-chloro-3-pyridazinyl)acetamide, the filtrate was extracted with ethyl acetate, and the extractant was removed by rotary evaporation , to obtain the crude product, then recrystallize the mixture of ethyl acetate and n-hexane to obtain the pure product N-(6-chloro-3-pyridazinyl)acetamide, after drying, the calculated yield is 70.39%, and the purity is 98.75% (HPLC ), NMR analysis: 1 HNMR (400Hz, deuterated DMSO) δ: 2.15(s, 3H), 7.87(d, 1H), 8.39(d, 1H), 11.31(s, 1H)...

Embodiment 2

[0019] Add 3-amino-6-chloropyridazine (1.30g, 10mmol), glacial acetic acid (1.20g, 20mmol) and 20mL (15.8g) ethanol in a 100ml single-necked round bottom flask, start the magnetic stirrer, and the The mixture was stirred and reacted at 90°C for 10 hours. TLC and GC detection confirmed that the reaction of raw material 3-amino-6-chloropyridazine was complete. The reaction solution was suction filtered, and the filter cake was recrystallized from a mixture of ethyl acetate and n-hexane to obtain the pure product N-(6-chloro-3-pyridazinyl)acetamide, the filtrate was extracted with ethyl acetate, and the extractant was removed by rotary evaporation , Obtain crude product, then obtain pure product N-(6-chloro-3-pyridazinyl) acetamide with the mixture recrystallization of ethyl acetate and normal hexane, after drying, calculate yield 75.80%, purity 99.00% (HPLC ).

Embodiment 3

[0021] Add 3-amino-6-chloropyridazine (12.96g, 100mmol), glacial acetic acid (9.00g, 150mmol) and 190mL (149g) acetonitrile in a 500ml single-necked round bottom flask, start the magnetic stirrer, and the mixture in the reaction flask The reaction was stirred at 90°C for 10 hours. TLC and GC detection confirmed that the reaction of raw material 3-amino-6-chloropyridazine was complete. The reaction solution was suction filtered, and the filter cake was recrystallized from a mixture of ethyl acetate and n-hexane to obtain the pure product N-(6-chloro-3-pyridazinyl)acetamide, the filtrate was extracted with ethyl acetate, and the extractant was removed by rotary evaporation , to obtain the crude product, then recrystallize the mixture of ethyl acetate and n-hexane to obtain the pure product N-(6-chloro-3-pyridazinyl)acetamide, after drying, the calculated yield is 73.10%, and the purity is 98.62% (HPLC ).

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Abstract

The invention relates to the field of organic matter synthesis and particularly discloses a synthetic method of N-(6-chloro-3-pyridazinyl) acetamide. The synthetic method comprises the following steps: taking 3-amino-6-chloropyridazine and glacial acetic acid as raw materials, wherein the ratio of 3-amino-6-chloropyridazine to glacial acetic acid is 1:(1.5-8.0); continuously conducting reaction for 5-18 hours at a temperature of 30-120 DEG C in one or two of acetonitrile, DMF, methanol, ethyl acetate, ethanol and 1,4-dioxane to generate a N-(6-chloro-3-pyridazinyl) acetamide crude product and purifying to obtain pure N-(6-chloro-3-pyridazinyl) acetamide. The synthetic method disclosed by the invention has the advantages that raw materials are easier to obtain, the price is reasonable, the reaction is mild, no special requirement for reaction equipment is made, ordinary corrosion-resistant equipment can be used for production, the reaction is easy to control, the post-treatment is simple, the product purity is high, and the popularization is easy.

Description

[0001] (1) Technical field [0002] The invention relates to the field of organic compound synthesis, in particular to a synthesis method of N-(6-chloro-3-pyridazinyl)acetamide. [0003] (2) Background technology [0004] N-(6-chloro-3-pyridazinyl)acetamide is an important organic intermediate widely used in the synthesis of medicines, pesticides, dyes and colorants, rubber accelerators and chemical reagents. This product has great value , its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports. [0005] (3) Contents of the invention [0006] In order to make up for the defects of the prior art, the present invention provides a synthetic method of N-(6-chloro-3-pyridazinyl)acetamide which is simple and reasonable in process, low in cost, high in product purity and suitable for industrialization. [0007] The present invention is achieved through the following technical solutions: [0008] A kind of synthetic met...

Claims

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Application Information

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IPC IPC(8): C07D237/20
CPCC07D237/20
Inventor 耿宣平来超来子腾来新胜
Owner 陕西友帮生物医药科技有限公司
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