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Synthesis method of 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine

A dihydropyridine and synthesis method technology, applied in 2 fields, can solve problems such as environmental impact, long reaction cycle, and complicated post-processing, and achieve the effects of mild reaction conditions, reduced preparation costs, and reduced cumbersome steps

Active Publication Date: 2012-07-18
山东润华兽药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] After analyzing and comparing the above-mentioned technical routes, it can be seen that: in method 1), the reaction conditions are mild, but the yield is low, and simultaneously raw material ammonia and formaldehyde all have larger irritating odor and toxicity, which easily cause work environment pollution; method 2) although the yield High, but the reaction cycle is too long, the energy consumption is large, the aftertreatment is complicated, and the cost is high; Method 3) The synthetic route has short reaction time, high yield, and relatively high energy consumption for steaming out the solvent, but due to the strong ammonia water in the production process The smell is very strong, which is very irritating to the workshop personnel and has a certain impact on the environment

Method used

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  • Synthesis method of 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine
  • Synthesis method of 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine
  • Synthesis method of 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine

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Effect test

Embodiment 1

[0030] Example 1, Preparation of 2,6-dimethyl-3,5-diethyl ester-1,4-dihydropyridine

[0031] Add urotropine 50g, ammonium acetate 25g and ethyl acetoacetate 300g into 500g water, under the condition of temperature 70 ℃, slowly add basic catalyst 6g (basic catalyst is NaOH and Na at 20 ℃) 2 CO 3 A saturated solution that is saturated, that is, the mass percentage concentration of NaOH is 52%, Na 2 CO 3 The mass percentage concentration of 24%), the dropwise addition was completed, the reaction was carried out for 60 min, and the temperature was rapidly lowered to 10 °C. After the reaction solution was cooled, the reaction solution was poured into ice water, filtered with suction, the filter cake was washed with water, and dried under vacuum at 60°C for 30 min to obtain the final product 2,6-dimethyl-3,5-diethyl ester Base-1,4-dihydropyridine 264.2g, product content 100.2%, yield 90.5%.

[0032] The H NMR spectrum of the product is shown in figure 1 shown. Depend on figur...

Embodiment 2

[0033] Example 2, Preparation of 2,6-dimethyl-3,5-diethyl ester-1,4-dihydropyridine

[0034] 50g of urotropine, 30g of ammonium acetate and 300g of ethyl acetoacetate were added to 550g of water, and under the condition of temperature 75°C, 9g of basic catalyst (basic catalyst was NaOH and Na at 20°C) was slowly added dropwise. 2 CO 3 A saturated solution that is saturated, that is, the mass percentage concentration of NaOH is 52%, Na 2 CO 3The mass percentage concentration of 24%), the catalyst was added dropwise within 50min, the reaction was performed for 45min, and the temperature was rapidly lowered to 15°C. After the reaction solution was cooled, the reaction solution was poured into ice water, filtered with suction, the filter cake was washed with water, and dried in vacuo at 65°C for 1 h to obtain the final product 2,6-dimethyl-3,5-diethyl ester 264.5 g of base-1,4-dihydropyridine, the product content was 101.0%, and the yield was 90.6%.

[0035] Its NMR analysis d...

Embodiment 3

[0037] Example 3, Preparation of 2,6-dimethyl-3,5-diethyl ester-1,4-dihydropyridine

[0038] 50 g of urotropine, 40 g of ammonium acetate and 350 g of ethyl acetoacetate were added to 600 g of purified water, and 14 g of basic catalyst (the basic catalyst was KOH and KHCO at 20 ° C) was slowly added dropwise at a temperature of 80 ° C. 3 A saturated solution that is saturated, that is, the mass percentage concentration of KOH is 26%, KHCO 3 The mass percentage concentration of 28%), the catalyst was added dropwise within 30 minutes, the reaction was performed for 30 minutes, and the temperature was rapidly lowered to 15 °C. After the reaction solution was cooled, the reaction solution was poured into ice water, filtered with suction, the filter cake was washed with water, dried under vacuum at 70 °C for 50 min, and the final product 2,6-dimethyl-3,5-diethyl ester was obtained 308.9 g of base-1,4-dihydropyridine, the product content is 100.5%, and the yield is 90.7%.

[0039]...

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Abstract

The invention provides a synthesis method of 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine shown in a formula (1). The 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine is a novel multifunctional feed additive and has an anti-oxidation function. The synthesis method comprises the following step of reacting urotropine, ethyl acetoacetate and ammonium acetate in a solvent in the presence of an alkaline catalytic system to obtain the 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine. The alkaline catalytic system is a 20-25 DEG C saturation solution of strong or weak alkaline. The 2,6-dimethyl-3,5-dicarbethoxy-1,4-dihydropyridine produced by using the synthesis method is aromatic and free of penetrating smell, has favorable palatability and is suitable for being used as feed additives inthe animal husbandry.

Description

technical field [0001] The invention relates to a method for synthesizing 2,6-dimethyl-3,5-diethyl ester-1,4-dihydropyridine, and belongs to the field of organic synthesis. Background technique [0002] 2,6-Dimethyl-3,5-diethyl ester-1,4-dihydropyridine is a new type of multifunctional feed additive with antioxidant effect, which can improve the activity of 6-phosphoglucose enzyme in biofilms , maintain the normal structure and function of the cell membrane system, increase the activity of serum superoxide dismutase (SOD), inhibit the oxidation of lipid molecules in the plasma membrane, protect the cell surface receptors and cell organelles, and maintain the integrity of the biofilm, Improve body immunity. It can protect the vitamins A, E and carotene in the feed and prevent the oxidative rancidity of the fat in the feed; it can increase the serum levels of thyroid hormone (T3), follicle-stimulating hormone (FSH), luteinizing hormone (LH) and other important hormones that r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/90A23K1/16A23K20/132
Inventor 王兵卢萍姚良峰
Owner 山东润华兽药有限公司
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