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A kind of methyl n-tetradecyl ethylimide and synthetic method thereof

A technology of methyl tetradecyl acetimidate and a synthetic method, which is applied in the field of organic synthesis and synthesis, can solve problems such as complex reaction process, cumbersome operation, and no public literature report on the production method, and achieve high yield and high production efficiency. The process method is simple and the effect of filling the blank of production technology

Active Publication Date: 2019-07-09
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the unsaturated system synthesis method and the triethyl orthoformate method, the imidate yield is low; while the Schmidt reaction process is complicated and the operation is cumbersome
[0014] And, the synthetic method of above N-substituted imidate is mainly limited to the target product of the functional group of short carbon chain, and for the imidic acid methyl ester of long carbon chain such as N-tetradecyl ethylimidic acid methyl ester The production method has not been reported in the public literature so far

Method used

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  • A kind of methyl n-tetradecyl ethylimide and synthetic method thereof
  • A kind of methyl n-tetradecyl ethylimide and synthetic method thereof
  • A kind of methyl n-tetradecyl ethylimide and synthetic method thereof

Examples

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Embodiment 1

[0036] This embodiment provides a kind of methyl N-tetradecyl acetimidate, which is synthesized through the following steps:

[0037] Weigh 2.22g of tetradecylamine into a four-neck flask equipped with a condenser, vacuum device and thermometer, add 30mL of methanol, and heat in a constant temperature oil bath until tetradecylamine is completely dissolved;

[0038] When the temperature rises to 70°C, slowly drop 1.72g of N,N-dimethylacetamide dimethyl acetal into the solution, and react for 130min at 0.1MPa;

[0039] TLC (V CHCl3:CH3OH =3:1) sample climbing board, no raw material point occurs, indicating that tetradecylamine is fully converted;

[0040] Reduce the pressure to 0.04MPa, and continue the reaction at 45°C for 25 minutes to obtain a light yellow liquid product, namely methyl N-tetradecylglycolimate, the yield of methyl N-tetradecylglycolimate was 72.2%.

[0041] The mass spectrogram (diluted in acetonitrile) of the product synthesized in this embodiment is as fo...

Embodiment 2

[0046] This embodiment provides a kind of methyl N-tetradecyl acetimidate, which is synthesized through the following steps:

[0047] Weigh 2.32g of tetradecylamine into a four-neck flask equipped with a condenser, vacuum device and thermometer, add 35mL of methanol, and heat in a constant temperature oil bath until tetradecylamine is completely dissolved;

[0048] When the temperature rises to 40°C, slowly drop 1.89g of N,N-dimethylacetamide dimethyl acetal into the solution, and react at 0.1MPa for 18h;

[0049] TLC (V CHCl3:CH3OH =3:1) sample climbing board, no raw material point occurs, indicating that tetradecylamine is fully converted;

[0050] Reduce the pressure to 0.05MPa, continue the reaction at 50°C for 20 minutes, and obtain a light yellow liquid product, which is methyl N-tetradecylglycolimate, the N-tetradecylglycolimate methyl ester of this example The yield of ester was 72.5%.

[0051] The above examples illustrate that in the synthetic method of N-tetradec...

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Abstract

The invention provides methyl N-tetradecyl acetimidate and a synthesis method thereof. The synthesis method comprises the following steps: dissolving acetal and tetradecylamine into methanol, wherein the molar ratio of acetal to tetradecylamine is (1: 1) to (1.5: 1) and the weight of methanol is 50-99% of the total weight; heating to the specified temperature, and reacting for 0.1-12 h under the atmospheric pressure; and reducing the pressure to 0.01-0.08 MPa, reacting for 0.25-12 h at 20-120 DEG C, and stopping the reaction to obtain methyl N-tetradecyl acetimidate. The invention further provides methyl N-tetradecyl acetimidate synthesized by the synthesis method. The yield of N-substituted imidoester synthesized by the synthesis method of methyl N-tetradecyl acetimidate can reach 72% or above, operation is simple, and the volatile product is easy to recycle and environment-friendly.

Description

technical field [0001] The invention relates to a synthesis method, in particular to a synthesis method of N-tetradecylglycolimate methyl ester, which belongs to the technical field of organic synthesis. Background technique [0002] N-substituted imidate is an important class of organic synthesis intermediates, and is also an important raw material for pharmaceutical research and development. The main intermediates of compounds such as (PataiS, Rappoport Z. The Chemistry of amidines and imidates [M]. Wiley, 1975). [0003] At present, the synthesis of N-substituted imidate compounds includes: [0004] Pinner reaction: under the catalysis of acid (such as hydrochloric acid), nitrile and alcohol generate imidate hydrochloric acid, which reacts with amine to generate N-substituted imidate compound (Jiang Hu, Liu Yin, Liu Xiaole, etc. N-cyanide A new method for the synthesis of ethyl ethyl imidate [J]. Applied Chemical Industry, 2013, 42(2): 274-278). [0005] [0006] Al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/08C07C249/02
CPCC07C249/02C07C251/08
Inventor 侯庆锋郭东红赵玉军徐艳王帆
Owner PETROCHINA CO LTD
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