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Preparation method of 2-methoxyethylamine

A technology of methoxyethylamine and methoxyethyl, which is applied in the field of synthesis of 2-methoxyethylamine, can solve problems such as difficult industrial production, cumbersome reaction routes, and equipment corrosion, and achieve simple operation and preparation The effect of simple route and mild reaction conditions

Pending Publication Date: 2021-05-07
GAOYOU CITY ORGANIC CHEM FACOTRY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] (2) David Milstein et al., in toluene solution, 2-methoxyethanol was catalyzed by ruthenium (Ru) metal ligands to oxidize 2-methoxyethanol to form 2-methoxyacetaldehyde and form imine intermediates with ammonia, followed by ligand Insertion and ligand exchange reactions prepare 2-methoxyethylamine; the reaction is simple to operate and has a high yield of 94%, but it needs to use expensive metal Ru to prepare ligands, which is costly and difficult for industrial production
[0013] The reaction yield is relatively high, which is 84%, but the reaction route is relatively cumbersome, and sodium hydroxide needs to be used, which is corrosive to the equipment

Method used

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  • Preparation method of 2-methoxyethylamine
  • Preparation method of 2-methoxyethylamine
  • Preparation method of 2-methoxyethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of 2-methoxyethylamine

[0030] In a 250ml round bottom flask, add N,N'-bis(2-methoxyethyl)thiourea (19.2g, 0.1mol), 40ml of acetonitrile, 120ml of water, potassium persulfate (81g, 0.3mol), Heat to reflux at 80°C for 6h (GC tracks the reaction progress); the reaction formula is as follows:

[0031]

[0032] After the reaction was finished, acetonitrile was distilled off; cooled to room temperature, added 100ml of pure water, extracted with dichloromethane (40ml*3), separated into layers, the organic phase was dried over anhydrous sodium sulfate and concentrated to obtain a crude product; purified by distillation (collecting 87 -90°C distillate) to obtain 12.525 g of pure product with a yield of 83.5%.

[0033] The H NMR and C NMR data of the product are as follows: 1 H NMR (400MHz, CDCl 3 )δ3.38(t, J=5.2Hz, 2H), 3.34(s, 3H), 2.82(t, J=5.2Hz, 2H), 1.56(s, 2H).

[0034] 13 C NMR (100MHz, CDCl 3 )δ77.03,58.91,41.94.

[0035] The str...

Embodiment 2

[0037] Embodiment 2: the screening of oxidizing agent

[0038] Experimental conditions of the present embodiment, charging amount are identical with embodiment 1, select different oxidant (3 times (molar ratio) of raw material II) to carry out experiment, specifically as shown in table 1:

[0039] Table 1

[0040] oxidizing agent yield 1 tert-butanol peroxide 46.2％ 2 hydrogen peroxide 13.5％ 3 potassium persulfate 83.5％ 4 sodium persulfate 78.3％

[0041] As can be seen from Table 1, when hydrogen peroxide is selected as oxidant, the reaction yield is the lowest, only 13.5%. Is 83.5%; In summary, the present invention preferably potassium persulfate as reaction oxidant.

Embodiment 3

[0042] Embodiment 3: potassium persulfate (K 2 S 2 o 8 ) dosage screening

[0043] The experimental conditions of the present embodiment, the feeding amount are identical with embodiment 1, select different doses of K 2 S 2 o 8 Carry out the experiment, specifically as shown in Table 2:

[0044] Table 2

[0045] Dosage (mol) yield 1 0.1 58.5％ 2 0.2 71.3％ 3 0.3 83.5％ 4 0.4 84.0％

[0046] As seen from Table 2, when the consumption of potassium persulfate was 0.1mol, the reaction yield was only 58.5%; when the consumption was 0.3mol, the reaction yield was 83.5%. Efficiency does not obviously improve; In sum, the present invention selects 0.3mol potassium persulfate optimally.

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Abstract

The invention relates to a preparation method of 2-methoxyethylamine in the technical field of organic synthesis chemical industry. The preparation method comprises the following steps: dissolving N,N'-bis(2-methoxyethyl)thiourea as an initial raw material in a solvent, and carrying out an oxidation reaction in the presence of an oxidant to prepare 2-methoxyethylamine. The method provided by the invention has the advantages of short route steps, mild conditions and high product yield, and provides a universal new method for preparation of 2-methoxyethylamine.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and chemical engineering, and in particular relates to a new method for synthesizing 2-methoxyethylamine. Background technique [0002] 2-Methoxyethylamine (formula I) is an important chemical raw material with good nucleophilic properties and relatively active chemical properties. It is widely used in chemical pharmaceuticals, polymer materials, flame retardants, metal ligands and Fine chemicals and other industries. For example, 2-methoxyethylamine can be used to synthesize tankyrase inhibitors with anticancer activity (formula III), prepare metal ligands with good catalytic effect (formula IV), and synthesize Functional material intermediates (formula Ⅵ), etc. [0003] [0004] At present, the 2-methoxyethylamine preparation method of bibliography mainly contains following several kinds: [0005] (1) In 1951, James et al. prepared 2-methoxyethylamine by alkaline hydrolysis of Ga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/08
CPCC07C213/02C07C217/08
Inventor 瞿军吴宏祥掌鹏程沈润溥
Owner GAOYOU CITY ORGANIC CHEM FACOTRY
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