Methyl N-dodecyl acetimidate and synthesis method thereof

A technology of methyl dodecyl acetimidate and a synthetic method, which is applied in the field of synthesis and organic synthesis, can solve the problems of 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: 2017-12-15
PETROCHINA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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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-dodecyl ethylimidic acid methyl ester The production method has not been reported in the public literature so far

Method used

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  • Methyl N-dodecyl acetimidate and synthesis method thereof
  • Methyl N-dodecyl acetimidate and synthesis method thereof
  • Methyl N-dodecyl acetimidate and synthesis method thereof

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Embodiment 1

[0036] This embodiment provides a kind of N-dodecyl acetimidic acid methyl ester, which is synthesized through the following steps:

[0037] Weigh 1.89g of dodecylamine into a four-necked flask with a condenser, vacuum device and thermometer, add 20mL of methanol, and heat in a constant temperature oil bath until dodecylamine is completely dissolved;

[0038] When the temperature rises to 70°C, slowly drop 1.70g of N,N-dimethylacetamide dimethyl acetal into the solution, and react at 0.1MPa for 180min;

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

[0040] Reduce the pressure to 0.01MPa, and continue the reaction at 60°C for 30 minutes to obtain a light yellow liquid product, namely methyl N-dodecylglycolimate, the yield of methyl N-dodecylglycolimate was 71.4%.

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

Embodiment 2

[0046] This embodiment provides a kind of N-dodecyl acetimidic acid methyl ester, which is synthesized through the following steps:

[0047] Weigh 1.92g of dodecylamine into a four-necked flask with a condenser, a vacuum device and a thermometer, add 30mL of methanol, and heat in a constant temperature oil bath until dodecylamine is completely dissolved;

[0048] When the temperature rises to 40°C, slowly drop 1.60g of N,N-dimethylacetamide dimethyl acetal into the solution, and react for 10h at 0.1MPa;

[0049] TLC (V CHCl3:CH3OH =3:1) spotting climbs the board, no raw material point occurs, indicating that dodecylamine is fully converted;

[0050] Reduce the pressure to 0.03MPa, continue the reaction at 50°C for 1h, and obtain a light yellow liquid product, which is methyl N-dodecylglycolimate, the N-dodecylglycolimate methyl ester of this example The yield of ester was 72.2%.

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

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Abstract

The invention provides methyl N-dodecyl acetimidate and a synthesis method thereof. The synthesis method comprises the following steps: dissolving acetal and dodecylamine into methanol, wherein the molar ratio of the acetal to the dodecylamine 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-dodecyl acetimidate. The invention further provides methyl N-dodecyl acetimidate synthesized by the synthesis method. The yield of N-substituted imidoester synthesized by the synthesis method of methyl N-dodecyl acetimidate can reach 71% 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 methyl N-dodecyl acetimidate, 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] Alkylation...

Claims

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Application Information

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