Synthesis method of organic compound of diamine monoselenide

A technology of organic compounds and diamine-based monos is applied in the field of synthesizing diamine-based monoselenide organic compounds, can solve problems such as few reports on synthetic methods, and achieve the effects of high scientific research value, low cost of raw materials, and high yield

CN106977438AInactive Publication Date: 2017-07-25SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2017-07-25
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a synthesis method of an organic compound of diamine monoselenide, and relates to a synthesis method of a compound, the method comprises the following steps: 1) protection of ethylethanolamine, to be more specific, using di-tert-butyl dicarbonate for protection of the ethylethanolamine; 2) hydroxy acylation, to be more specific, using one or a mixture of two of paratoluensulfonyl chloride and Phthaloyl dichloride as a hydroxyacylating agent; 3) reaction with sodium hydrogen selenide to obtain a single selenium bridged compound, and deprotection; and 4) extraction with an organic solvent to obtain the diamine monoselenide. A diamine monoselenium compound with protective group BOC is prepared from the ethylethanolamine as a raw material by (BOC) 2O protection, hydroxyl sulfonation reaction and reaction with the sodium hydrogen selenide by the method, and finally the diamine monoselenide compound can be obtained by treating with trifluoroacetic acid. The method has the advantages of low raw material cost, easy obtaining, simple preparation, easy control, high yield and high scientific research value.
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Description

technical field

[0001] The invention relates to a synthesis method of a compound, in particular to a synthesis method of a diamino monoselenide organic compound. Background technique

[0002] Selenium is a special trace element that has an anticancer effect on the human body. In recent years, selenium-containing compounds have attracted more and more attention. At present, a variety of synthetic methods of selenium-containing compounds have been reported, but there are few reports on the synthetic methods of diaminomonoselenide organic compounds. Contents of the invention

[0003] The object of the present invention is to provide a kind of synthetic method of diamine-based monoselenide organic compound, and the inventive method is to be raw material with ethyl ethanolamine group, through (BOC) 2 O protection, hydroxyl sulfonation and reaction with sodium selenium hydride to obtain a diamine monoselenium compound with a protective group BOC, and finally treated with triflu...

Examples

preparation example Construction

[0021] The invention is a simple and efficient synthesis method of diamine monoselenide. The synthesis steps are as follows:

[0022] 1) Use ethyl ethanolamine (BOC) 2 O protection.

[0023] 2) Acylation of its hydroxyl group.

[0024] 3) Reaction with sodium selenium hydride to obtain a monoselenide bridging compound, and then remove the BOC protecting group with trifluoroacetic acid.

[0025] 4) extracting with an organic solvent to obtain diamine monoselenide.

[0026] Add di-tert-butyl dicarbonate dropwise to ethyl ethanol, the dosage ratio is 1:1.5, this method has sufficient reaction and high yield. Above-mentioned step 3) is anaerobic operation under ice bath condition, and reaction is more fully, and by-product is few. After removing the BOC protecting group with trifluoroacetic acid, the product was dissolved in an alkaline solution to form a salt.

[0027] The solvents used in the present invention are all organic solvents, and dichloromethane, ethyl acetate, m...

Embodiment 1

[0030] To a 250ml round bottom flask was added 4.5g ethylethanolamine (0.05mol) and dissolved in 50ml dichloromethane.

[0031] At 30° C., 16.37 g of di-tert-butyl dicarbonate (0.75 mol) dissolved in 50 ml of dichloromethane was slowly added dropwise into the round bottom flask, and the dropwise addition continued for 1 hour.

[0032] After the dropwise addition was complete, it was stirred at room temperature for 12 hours. After the reaction was completed, the dichloromethane solution was extracted three times each with 300ml of 0.1mol hydrochloric acid, 300ml of 5% sodium bicarbonate solution, and 300ml of saturated sodium chloride solution. The organic phase was dried with anhydrous sodium sulfate, then filtered, and the organic phase was spin-dried under reduced pressure with a rotary evaporator to obtain a transparent liquid compound 1 (9.4 g, yield 99.3%).

[0033] The structural formula of compound 1 is as follows:

[0034]

[0035] δ H (500 MHz; CDCl 3 ) 1.11 (...

Embodiment 2

[0055] To a 250ml round bottom flask was added 4.5g ethylethanolamine (0.05mol) and dissolved in 50ml dichloromethane.

[0056] Under the condition of 30° C., 10.91 g of di-tert-butyl dicarbonate (0.05 mol) dissolved in 50 ml of dichloromethane was slowly added dropwise into the round bottom flask, and the dropwise addition continued for 1 hour.

[0057] After the dropwise addition was complete, it was stirred at room temperature for 12 hours. After the reaction was completed, the dichloromethane solution was extracted three times each with 300ml of 0.1mol hydrochloric acid, 300ml of 5% sodium bicarbonate solution, and 300ml of saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate,

[0058] Into a 250ml round bottom flask was added 4g of compound 1 (21.2mmol) dissolved in 50ml of dry dichloromethane, and then 8.8ml of triethylamine (63.5mmol) was added to the solution.

[0059] 4.04 g of p-toluenesulfonyl chloride (21.2 mmol) dissolved...