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Synthetic method of 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione

A technology of triazacyclononane and synthesis method, applied in the direction of organic chemistry, etc.

Active Publication Date: 2022-03-18
扬州市荣晶新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no published literature reporting this class of compounds and their synthetic methods

Method used

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  • Synthetic method of 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione
  • Synthetic method of 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione
  • Synthetic method of 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione

Examples

Experimental program
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Effect test

example 1

[0032] In a 1000ml four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer, 25.8g (0.2mol) of 1-(2-aminoethyl)-2-imidazolidinone, 1,2-dibromoethyl 37.5 g (0.2 mol) of alkane, 70 g (0.5 mol) of anhydrous potassium carbonate and 600 ml of acetonitrile. After the addition was complete, it was stirred at room temperature for 12 hours.

[0033] Then the oil bath was heated to reflux, the reflux temperature was 85° C., and the reflux was kept for 144 hours.

[0034] After keeping warm, cool to room temperature. Filtration, the filter cake is the reaction by-product potassium bromide and excess potassium carbonate. Rinse the filter cake with 100ml of fresh acetonitrile, and combine the filtrate and washings. The acetonitrile was evaporated under reduced pressure with a rotary evaporator, and the obtained orange-red oily liquid was heated to boiling by adding 100 ml of methanol, and then refrigerated overnight to precipitate white flaky crystals. ...

example 2

[0036] In a 1000ml four-necked flask equipped with a mechanical stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer, 600ml of N,N-dimethylformamide, 56g of N,N-diisopropylethylamine (0.43 mol), 1-(2-aminoethyl)-2-imidazolinone 25.8g (0.2mol), 1,2-dibromoethane 37.5g (0.2mol). After the addition was complete, it was stirred at room temperature for 12 hours.

[0037] Then the oil bath was heated to 100 degrees to keep warm for 48 hours.

[0038] After the heat preservation is over, transfer the reaction solution to a rotary evaporator and rotary evaporate under reduced pressure. After evaporating the solvent, add 500ml of dichloromethane and 100ml of water to the residue in the bottle and stir for 10 minutes. Separate the water layer and wash the oil layer with 100ml of water twice . The oil layer washed with water was dried over anhydrous sodium sulfate, and dichloromethane was distilled off to obtain a light yellow solid. It was recrystallized...

example 3

[0041] In a 1000ml four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer, 29g (0.2mol) of 1-(2-aminoethyl)-2-imidazolinthione, 1,2-dichloroethyl 19.8g (0.2mol) of alkane, 50.5g (0.5mol) of triethylamine, 2.5g of potassium iodide and 600ml of acetonitrile. After the addition was complete, it was stirred at room temperature for 72 hours.

[0042] Then the oil bath was heated to reflux, the reflux temperature was 84° C., and the reflux was kept for 96 hours.

[0043] After the heat preservation is over, transfer the reaction solution to a rotary evaporator and rotary evaporate under reduced pressure. After evaporating the solvent, add 500ml of dichloromethane and 100ml of water to the residue in the bottle and stir for 10 minutes. Separate the water layer and wash the oil layer with 100ml of water twice . The oil layer washed with water was dried over anhydrous sodium sulfate, and dichloromethane was distilled off to obtain a light yellow so...

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Abstract

The invention proposes a synthesis method of 1,4,7-triazacyclononane-1,4-ketone and 1,4,7-triazacyclononane-1,4-thione. 1,4,7‑Triazacyclononane‑1,4‑one and 1,4,7‑Triazacyclononane‑1,4‑thione are new compounds that can be used as 1,4,7‑ An important synthetic intermediate of triazacyclononane and its derivatives. In the present invention, 1-(2-aminoethyl)-2-imidazolinone compounds are condensed with 1,2-dihalogenated ethane compounds to obtain products, namely 1,4,7-triazacyclononane- 1,4-ketone and 1,4,7-triazacyclononane-1,4-thione. The process of the invention has the advantages of low raw material cost, high conversion rate, mild reaction conditions, simple and easy-to-control reaction process, high purity of the final product, and the like.

Description

technical field [0001] The invention proposes a synthesis method of 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione. Background technique [0002] 1,4,7-Triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione are new compounds that can be used as 1,4,7- An important synthetic intermediate of triazacyclononane and its derivatives. At present, there is no published literature reporting this type of compound and its synthesis method. [0003] The molecular structural formulas of 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione are: [0004] Contents of the invention [0005] The object of the present invention is to provide a method for synthesizing 1,4,7-triazacyclononane-1,4-one and 1,4,7-triazacyclononane-1,4-thione. [0006] The object of the present invention is achieved through the following technical solutions, a kind of 1,4,7-triazacyclononane-1,4-ketone and 1,4,7-triazacyclononane-1,4-thione resolve resolut...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/08
CPCC07D487/08
Inventor 邹从伟张燕李付
Owner 扬州市荣晶新材料科技有限公司
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