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

A technology of dihydropyridine and a synthesis method, applied in 2 fields, can solve problems such as long reaction period, complicated post-processing, environmental impact, etc., and achieve the effects of reducing preparation cost, reducing tedious steps, and mild reaction conditions

Active Publication Date: 2011-02-16
山东润华兽药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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Embodiment 1

[0030] Embodiment 1, the preparation of 2,6-dimethyl-3,5-carbocarboxylate-1,4-dihydropyridine

[0031] Hexatropine 50g, ammonium acetate 25g and ethyl acetoacetate 300g are joined in 500g water, under the condition of temperature 70 ℃, dropwise basic catalyst 6g (basic catalyst is NaOH and NaOH at 20 ℃ 2 CO 3 Both reach the saturated saturated solution, that is, the mass percent concentration of NaOH is 52%, and NaOH 2 CO 3 The mass percent concentration of 24%), after the dropwise addition, reacted for 60 minutes, and quickly cooled down to 10°C. After the reaction solution is cooled, pour the reaction solution into ice water, filter with suction, wash the filter cake with water, and dry it in vacuum at 60°C for 30 minutes to finally obtain the 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 figure 1 It can be seen that the obtai...

Embodiment 2

[0033] Embodiment 2, the preparation of 2,6-dimethyl-3,5-carbocarboxylate-1,4-dihydropyridine

[0034] Hexatropine 50g, ammonium acetate 30g and ethyl acetoacetate 300g are joined in 550g water, under the condition of temperature 75 ℃, slowly dropwise basic catalyst 9g (basic catalyst is NaOH and NaOH at 20 ℃ 2 CO 3 Both reach the saturated saturated solution, that is, the mass percent concentration of NaOH is 52%, and NaOH 2 CO 3The mass percentage concentration of 24%), the catalyst was added dropwise within 50 minutes, reacted for 45 minutes, and rapidly cooled down to 15°C. After the reaction solution is cooled, pour the reaction solution into ice water, filter with suction, wash the filter cake with water, and dry it under vacuum at 65°C for 1 hour to finally obtain the product 2,6-dimethyl-3,5-diethyl ester 264.5 g of base-1,4-dihydropyridine, the product content is 101.0%, and the yield is 90.6%.

[0035] Its NMR analysis data: 1 H NMR (CDCl 3 , 300MHz): δ1.40(t, ...

Embodiment 3

[0037] Embodiment 3, the preparation of 2,6-dimethyl-3,5-carbocarboxylate-1,4-dihydropyridine

[0038] Add 50 g of urotropine, 40 g of ammonium acetate and 350 g of ethyl acetoacetate into 600 g of purified water, and slowly add 14 g of basic catalyst (basic catalyst is KOH and KHCO at 20 °C) under the condition of 80 ° C. 3 Both reach saturated saturated solution, that is, the mass percent concentration of KOH is 26%, KHCO 3 The mass percent concentration is 28%), the catalyst is added dropwise within 30 minutes, reacted for 30 minutes, and rapidly cooled to 15°C. After the reaction solution is cooled, pour the reaction solution into ice water, filter with suction, wash the filter cake with water, and dry it in vacuum at 70°C for 50 minutes to finally obtain the product 2,6-dimethyl-3,5-diethyl ester 308.9 g of base-1,4-dihydropyridine, the product content is 100.5%, and the yield is 90.7%.

[0039] Its NMR analysis data: 1 H NMR (CDCl 3 , 300MHz): δ1.39(t, 6H, -CH 2 C...

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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 in the animal husbandry.

Description

technical field [0001] The invention relates to a synthesis method of 2,6-dimethyl-3,5-dicarboethoxy-1,4-dihydropyridine, belonging to the field of organic synthesis. Background technique [0002] 2,6-Dimethyl-3,5-dicarboethoxy-1,4-dihydropyridine is a new multifunctional feed additive with antioxidant effect and can increase the activity of 6-phosphoglucose in biofilm , 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 cell surface receptors and cell organelles, maintain the integrity of the biomembrane, Improve the body's immunity. It can protect the vitamin A, E and carotene in the feed, prevent the oxidative rancidity of the fat in the feed; it can increase the levels of important hormones that regulate production such as thyroid hormone (T3), follicle-stimulating hormone (FSH), and luteinizing hormone (LH) in serum ,...

Claims

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Application Information

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Patent Type & Authority Applications(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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