Novel compound 6-fluoro-2,4-diamino-nitrobenzene and preparation method thereof

A technology for trifluoronitrobenzene and compounds, which is applied in the field of new compound 6-fluoro-2,4-diaminonitrobenzene and its preparation, and can solve the problem of high cost, low yield and limited fluorine-containing nitroaniline The application needs of aromatic compounds, etc., to achieve the effect of mild reaction, easy handling and purification

Inactive Publication Date: 2018-12-28
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the preparation of similar compounds generally needs to be prepared under high temperature and high pressure or requires expensive metal catalysts, and the yield is not high and the cost is high, which greatly limits the application needs of fluorine-containing nitroaniline aromatic compounds

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The preparation method of 6-fluoro-2,4-diaminonitrobenzene of the present embodiment is as follows:

[0018] Add 67.0g (0.378mol) of 2,4,6-trifluoronitrobenzene into a 1000ml single port, and add 250mL of ethanol to dissolve, then slowly add 209g (2.646mol) of ammonium bicarbonate, after the addition is complete and mix well, at 25 After standing at ℃ for 12 hours, crystals precipitated out of the system, filtered and washed with suction, and the crude product was recrystallized with ethanol / water (v:v) = 2:1 to obtain 61.1 g of light yellow crystals, with a yield of 94.5%;

[0019] MS: m / z: [M+1]:172

[0020] 1 H NMR (400 MHz, CDCl 3 ): δ 6.24 (d, 1H), 6.10 (br, 4H), 5.92 (s, 1H)

Embodiment 2

[0022] The preparation method of 6-fluoro-2,4-diaminonitrobenzene of the present embodiment is as follows:

[0023] Add 67.0g (0.378mol) of 2,4,6-trifluoronitrobenzene into a 1000ml single port, and add 250mL of ethanol to dissolve, then slowly add 239g (3.024mol) of ammonium bicarbonate, after the addition is complete and mix well, at 25 After standing at ℃ for 10 hours, the system precipitated crystals, which were filtered and washed with suction. The crude product was recrystallized with ethanol / water (v:v) = 2:1 to obtain 59.5 g of light yellow crystals, with a yield of 92%.

Embodiment 3

[0025] The preparation method of 6-fluoro-2,4-diaminonitrobenzene of the present embodiment is as follows:

[0026] Add 67.0g (0.378mol) of 2,4,6-trifluoronitrobenzene into a 1000ml single port, and add 250mL of ethanol to dissolve, then slowly add 179g (2.268mol) of ammonium bicarbonate, after the addition is complete and mix well, at 35 After standing at ℃ for 11 hours, the system precipitated crystals, which were filtered and washed with suction. The crude product was recrystallized with ethanol / water (v:v) = 2:1 to obtain 57.6 g of light yellow crystals, with a yield of 89.2%.

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PUM

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Abstract

The invention discloses a novel compound 6-fluoro-2,4-diamino-nitrobenzene and a preparation method thereof. The structural formula of 6-fluoro-2,4-diamino-nitrobenzene is shown in the description. The preparation method comprises steps as follows: 2,4,6-trifluoro-nitrobenzene is dissolved in ethanol, ammonium bicarbonate is added, the mixture is left to stand at the room temperature for 10-12 h,suction filtration, washing and recrystallization in an ethanol water solution are performed, and a canary yellow product, namely, 6-fluoro-2,4-diamino-nitrobenzene, is obtained. The preparation method is relatively mild in condition, and the product is easy to treat and purify and suitable for preparation in batches.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a novel compound 6-fluoro-2,4-diaminonitrobenzene and a preparation method thereof. Background technique [0002] Fluorine-containing nitroaniline aromatic compounds have become important raw materials for the synthesis of pesticides, medicines, dyes and other chemical fine chemicals due to their unique chemical and biological properties. For example, 2-fluoro-5-nitroaniline is an important pharmaceutical and pesticide intermediate, which can be used in the synthesis of antibacterial and anti-inflammatory and amidrazone herbicides. In addition, it can also play an important role in the textile industry as a dye intermediate . 6-Fluoro-2,4-diaminonitrobenzene is a very important class of compounds, because of its unique value, it can provide important reference information for the development of fluorine-containing nitroaniline aromatic compounds in pharmaco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/10
CPCC07C209/10C07C211/52
Inventor 靳清贤胡路平张洪培
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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