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Method for synthesizing hydrated dipyridino hexahydro triazine bromide salt

A technology for hydrating bipyridine bromide and hexahydrotriazine, which is applied in the synthesis of pyridine N-heterocycles and dibromomethane, and in the field of synthesizing hydrated bipyridino-hexahydrotriazine bromide, which can solve the problem that the yield is only 25%. Methyl iodide is expensive, highly toxic and other issues, to achieve the effect of high product yield

Inactive Publication Date: 2012-07-04
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the synthesis of nitrogen cyanine compounds from pyridine and pyridine compounds and dibromomethane. Only Haddadin et al. reported that 2-aminopyridine and diiodomethane were refluxed in acetonitrile solvent to obtain nitrogen cyanine, and the yield was only 25% (references: J. Org. Chem., Vol. 66, No. 4, 2001, 1310-1315), diiodomethane is not only expensive, but also has strong toxicity, and it is decomposed by heat to release toxic iodide fumes; the reaction is carried out in acetonitrile solution, which has a certain impact on subsequent processing

Method used

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  • Method for synthesizing hydrated dipyridino hexahydro triazine bromide salt
  • Method for synthesizing hydrated dipyridino hexahydro triazine bromide salt
  • Method for synthesizing hydrated dipyridino hexahydro triazine bromide salt

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Experimental program
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Effect test

Embodiment 1

[0021] Add 1.0002g of 2-aminopyridine into a 100mL flask, add 15.0mL of dibromomethane, connect the reflux device, and react in an oil bath at 110°C for 3 hours. After the reaction, cool the flask to room temperature. The remaining dibromomethane was distilled off under reduced pressure to obtain a bright yellow solid powder, which was dissolved in methanol and recrystallized at room temperature to obtain 1.5238 g of light yellow crystals with a yield of 90.20%.

Embodiment 2

[0023] Add 1.5332g of 5-bromo-2-aminopyridine into a 100mL flask, and add 10.0mL of dibromomethane, connect the reflux device, and react in an oil bath at 110°C for 3 hours. After the reaction, cool the flask to room temperature. The remaining dibromomethane was distilled off under reduced pressure, and 1.8390 g of light yellow solid powder was obtained after drying, with a yield of 87.25%.

Embodiment 3

[0025] 2. Add 0128g of 3,5-dibromo-2-aminopyridine into a 100mL flask, add 5.0mL of dibromomethane, connect the reflux device, and react in an oil bath at 120°C for 3 hours. After the reaction, cool the flask to room temperature. The remaining dibromomethane was distilled off under reduced pressure, and 2.0147 g of brown solid powder was obtained after drying, with a yield of 79.61%.

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Abstract

The invention discloses a method for synthesizing a hydrated dipyridino hexahydro triazine bromide salt. The method comprises the step of carrying out a reaction on 2-amino pyridine substances and dibromomethane under the reflux state so as to synthesize a series of nitrogen cyanine compounds. The nitrogen cyanine compounds synthesized by using the method can show absorption performance in an ultraviolet light-visible light region and have fluorescent properties. The method disclosed by the invention has the advantages of simple step and high yield, and is convenient.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to the synthesis technology of pyridine N-heterocycles and methylene bromide, in particular to a method for synthesizing hydrated brominated bipyridinohexahydrotriazine salts. Background technique [0002] Nitrocyanine compounds are triazine derivatives, specifically 1,3,5-triazine. S-triazine is a colorless crystal, which is produced by the reaction of hydrogen cyanide and hydrogen chloride. It can be used as a bactericidal agent in industrial production such as papermaking and coatings. agent use. S-triazine derivatives are also extremely important in the dye and pharmaceutical industries, such as triamine can be used as anticancer drugs. [0003] Pyridine and pyridine derivatives have high reactivity due to the existence of N element, and are widely used in the field of organic synthesis. Dihalomethanes also have high reactivity, as reported by Wamser et al. using...

Claims

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Application Information

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IPC IPC(8): C07D487/14
Inventor 单永奎孙卓东张恒强申欢欢
Owner EAST CHINA NORMAL UNIV
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