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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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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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