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Novel synthesis method of 1, 4, 7, 10-tetraazacyclododecane

A synthesis method and technology of tetranitrogen ring, applied in the direction of organic chemistry, etc., can solve the problems of low total molar yield, long process route, high production cost and the like

Active Publication Date: 2020-10-23
扬州市荣晶工业助剂有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has good atom economy, its process route is long, the total molar yield is low, and the production cost is high

Method used

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  • Novel synthesis method of 1, 4, 7, 10-tetraazacyclododecane
  • Novel synthesis method of 1, 4, 7, 10-tetraazacyclododecane
  • Novel synthesis method of 1, 4, 7, 10-tetraazacyclododecane

Examples

Experimental program
Comparison scheme
Effect test

example 1-1

[0040] Put 146g of triethylenetetramine (originally produced in Tosoh, Japan) (1mol) and 120g of urea (2mol) into a 2000ml reaction bottle equipped with a 300W motor stirring, insert a thermometer and connect the gas outlet to the exhaust gas treatment device. After the stirring is turned on, use a heating mantle to raise the temperature. When the temperature reaches 130°C, the material in the bottle suddenly expands and a large amount of ammonia gas escapes. Continue to heat up and keep warm at 150°C for half an hour. As the heat preservation proceeds, the material in the bottle gradually becomes dry powder, and the escaped gas gradually decreases until no more gas escapes. Remove the electric heating mantle, stir and drop to room temperature.

[0041] Add 1000ml of methanol aqueous solution with a mass fraction of 50% to the bottle, connect the tail gas port to a reflux condenser, and heat to boiling reflux in a water bath while stirring, and the reflux temperature is 64°C...

example 1-2

[0043] Put 146g of triethylenetetramine (originally produced in Tosoh, Japan) (1mol) and 132g of urea (2.2mol) into a 2000ml reaction bottle equipped with a 300W motor stirring, insert a thermometer and connect the gas outlet to the exhaust gas treatment device. After the stirring is turned on, use a heating mantle to raise the temperature. When the temperature reaches 130°C, the material in the bottle suddenly expands and a large amount of ammonia gas escapes. Continue to heat up and keep the temperature at 200°C for 10 minutes. As the heat preservation proceeds, the material in the bottle gradually becomes dry powder, and the escaped gas gradually decreases until no more gas escapes. Remove the electric heating mantle, stir and drop to room temperature.

[0044]Add 1000ml of methanol aqueous solution with a mass fraction of 50% to the bottle, connect the tail gas port to a reflux condenser, and heat to boiling reflux in a water bath while stirring, and the reflux temperatu...

example 2-1

[0047] Weigh 20 g of the bis-imidazolinone (0.1 mol) obtained in Example 1-1 and add it into 200 ml of ethyl acetate, stir and dissolve for later use.

[0048] Add 15g of 1,2-dichloroethane (0.15mol), 107g of cesium carbonate (0.33mol) and 800ml of ethyl acetate into a 2000ml flask equipped with a thermometer, dropping funnel and stirring, and cool with a dry ice acetone bath. When the temperature dropped to minus 30°C, the ethyl acetate solution of the aforementioned bis-imidazolidinone was added dropwise. Adjust the rate of addition so that the temperature of the system does not exceed minus 10°C. After the dropwise addition, keep the temperature between minus 10°C and 0°C for 5 hours.

[0049] After the heat preservation was completed, the reaction solution was poured out and filtered, and the filtrate was concentrated under reduced pressure to a volume of 100ml, and the concentrated solution was placed in a refrigerator to freeze overnight. The next day, flaky crystals w...

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Abstract

The invention provides a novel synthesis method of 1, 4, 7, 10-tetraazacyclododecane. The 1, 4, 7, 10-tetraazacyclododecane has important application in biomedicine and molecular biology, molecular recognition, catalysis, enzyme chemistry, supramolecular chemistry, hydrogen storage materials and other main surfaces. The preparation method comprises the following steps of: reacting triethylene tetramine and urea serving as initial raw materials to generate ethylene bis-imidazolinone (hereinafter referred to as bis-imidazolinone), carrying out condensation reaction on the raw material and 1, 2-dihalogenated ethane to generate 1, 4-keto-7, 10-keto-1, 4, 7, 10-tetraazacyclododecan (hereinafter referred to as diketone cyclododecane), and preparing 1, 4, 7, 10-tetraazacyclododecane by hydrolysis. According to the method, the product with the gas chromatography content of 99% or above is obtained at the highest total yield of 74.97%. The method has the advantages of high atom utilization rate, few reaction steps, simplicity, easiness in control, high yield and the like, and is a new process route representing clean and efficient production.

Description

technical field [0001] The invention proposes a new method for synthesizing 1,4,7,10-tetraazacyclododecane. Background technique [0002] Polyamines present in organisms are closely related to cell growth and cancer, and they can regulate the efficiency of in vitro transcription systems (eg, have an effect on in vitro transcription of T7 RNA polymerase). However, 1,4,7,10-tetraazacyclododecane, which is similar in structure to polyamines, can be covalently linked to biologically active molecules (such as antibodies or antibody fragments) after complexing with metal ions, so 1,4,7, 10-tetraazacyclododecane is becoming an important structural component of new drugs. [0003] 1,4,7,10-Tetraazacyclododecane is also the most versatile intermediate for lanthanide-specific chelators, mainly for compounds in diagnostic and therapeutic medicine, such as lanthanides for medical NMR Chelating agent. N-alkylation can also be carried out to prepare a variety of coordination compounds ...

Claims

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Application Information

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IPC IPC(8): C07D257/02C07D295/027C07D295/023
CPCC07D257/02C07D295/027C07D295/023
Inventor 张燕邹从伟李付
Owner 扬州市荣晶工业助剂有限公司
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