Synthetic method of fatty acid containing nitrogen heterocycle

A synthesis method and fatty acid technology, applied in chemical instruments and methods, carboxylate preparation, organic compound preparation, etc., can solve problems such as difficult storage, no practical application value, high price of organometallic reagents, etc. The method is simple and reliable Effect

Inactive Publication Date: 2018-06-29
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In addition, although the existing use of organometallic reagents and carbon dioxide reactions to prepare aromatic fatty acids, organometallic reagents are very re

Method used

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  • Synthetic method of fatty acid containing nitrogen heterocycle
  • Synthetic method of fatty acid containing nitrogen heterocycle

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0015] Example 1

[0016] The synthesis method of 6-chloro-3-pyridineacetic acid includes the following steps:

[0017] S1: Take 8.72mmol 2-chloro-5-chloromethylpyridine The catalyst and solvent DMF are added to the reactor;

[0018] S2: Feed carbon dioxide to make the pressure in the kettle 3MPa, and adjust the reaction to proceed at 40°C for 15 hours.

[0019] S3: Add dilute hydrochloric acid to the reaction kettle for acidification, extract with ethyl acetate, combine the organic phases, remove the liquid by rotary evaporation, and further dry in vacuum to obtain 6-chloro-3-pyridineacetic acid

[0020] The catalyst includes zinc powder and lithium chloride, chloromethyl heterocyclic compound and zinc powder, the molar ratio of lithium chloride added to the reactor is 1:3:3, per mmol of 2-chloro-5-chloromethylpyridine Add 2.8~2.9ml solvent DMF.

[0021] The nuclear magnetic resonance (1H NMR and 13C NMR) detection data of the compound 6-chloro-3-pyridineacetic acid of Example 1 are:...

Example Embodiment

[0028] Example 2

[0029] The synthetic method of 2-chloro-5-thiazole acetic acid includes the following steps:

[0030] S1: Take 8.72mmol 2-chloro-5-chloromethylthiazole The catalyst and solvent DMF are added to the reactor.

[0031] S2: Feed in carbon dioxide, make the pressure in the kettle 4MPa, adjust the reaction at 40°C for 16 hours;

[0032] S3: Add dilute hydrochloric acid to the reaction kettle for acidification, extract with ethyl acetate, combine the organic phases, remove the liquid by rotary evaporation, and further dry in vacuum to obtain 2-chloro-5-thiazoleacetic acid

[0033] The catalyst includes zinc powder and lithium chloride, chloromethyl heterocyclic compound and zinc powder, the molar ratio of lithium chloride added to the reactor is 1:3:3, per mmol of 2-chloro-5-chloromethylthiazole Add 2.8ml solvent DMF.

[0034] NMR of the compound 2-chloro-5-thiazoleacetic acid of Example 1 ( 1 H NMR and 13 C NMR) detection data:

[0035] 1 H NMR(400MHz, DMSO-d 6 ) δ 12.96 (...

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Abstract

The invention discloses a synthetic method of fatty acid containing nitrogen heterocycle. The synthetic method comprises the following steps: (S1) adding a heterocyclic compound with substitution of chloromethyl groups, a catalyst and a solvent DMF into a reaction kettle; (S2) introducing carbon dioxide to lead the pressure in the kettle to be 2-4MPa, adjusting and reacting for 10-16 hours at thetemperature of 40-50 DEG C; (S3) adding diluted hydrochloric acid into the reaction kettle to carry out acidification, using ethyl acetate for extraction, combining organic phases, carrying out rotaryevaporation to remove liquid, and further carrying out vacuum drying, thus obtaining the fatty acid containing nitrogen heterocycle. The synthetic method disclosed by the invention has the beneficialeffects that a one-pot method is adopted, the raw materials are easy to obtain, price is low, aftertreatment of products is also simpler, the universality for a substrate is also very high, and the promotion and application are easy.

Description

technical field [0001] The present invention relates to the field of synthesis of fatty acids. More specifically, the present invention relates to a method for synthesizing nitrogen-containing heterocyclic fatty acids. Background technique [0002] Nitrogen-containing heterocyclic fatty acids play an important role in the research of drug synthesis, such as ibuprofen and indole acetic acid, which have been used as drugs. CO 2 It is a gas that causes the greenhouse effect. It is rich in content and low in price and is often used as a carbon source for organic synthesis. However, due to CO 2 The inertness of the reaction limits its application. How to use CO 2 The study of synthetic fatty acid has important practical significance, and more and more people pay attention to it. [0003] In addition, although the existing use of organometallic reagents and carbon dioxide reaction to prepare aromatic fatty acids, organometallic reagents are very reactive and often easily reac...

Claims

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Application Information

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IPC IPC(8): C07D213/61C07D277/32C07C51/15C07C57/32C07C57/58C07C57/30C07C57/40C07C59/64C07C63/14C07C57/42C07C57/34C07C57/38
CPCC07D213/61C07C51/15C07D277/32C07C57/32C07C57/58C07C57/30C07C57/40C07C59/64C07C63/14C07C57/42C07C57/34C07C57/38
Inventor 张培培周宏伟刘小明邱观音生肖志音
Owner JIAXING UNIV
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