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Synthesis method for 2,2'-dinitryl diphenylethene

A technology of dinitrostilbene and synthesis methods, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of cumbersome steps, lack of supply of o-nitrophosphonate, etc., and achieve simple equipment , the reaction conditions are easy to control, and the process flow is short

Inactive Publication Date: 2012-08-08
JIANGSU TOHOPE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] Although this synthesis method avoids the bromine impurity, the starting material o-nitrophosphonate is short of supply in the market, and its own synthesis needs to introduce phosphoric acid and other raw materials that seriously pollute the water body, and the steps are cumbersome

Method used

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  • Synthesis method for 2,2'-dinitryl diphenylethene
  • Synthesis method for 2,2'-dinitryl diphenylethene
  • Synthesis method for 2,2'-dinitryl diphenylethene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Add 2.8g (0.02mol) of o-nitrotoluene, 3.1g (0.02mol) of o-nitrobenzaldehyde, and 0.5g (0.00155mol) of tetrabutylammonium bromide into a 100mL four-neck flask, then add 15mL of toluene and stir. And keep the temperature at 30~35°C, add dropwise 1.2g of 50% NaOH solution (containing 0.6g, 0.015molNaOH) for 1 hour, after the dropwise addition, add 0.2g (0.005mol) of solid sodium hydroxide, and continue the reaction for 5 ~12 hours. The reaction solution was washed with water to neutrality, the organic layer was evaporated toluene solvent under reduced pressure, and finally an appropriate amount of methanol solution was added to precipitate a solid product, which was filtered and dried to obtain 4.3 g of yellow solid 2,2'-dinitrostilbene, yield It is 79.6%, and the purity is more than 97%.

[0047] 1 HNMR (400MHz, CDCl 3 ): 7.46~7.50 (t, 2H), 7.57 (s, 2H), 7.65~7.69(t, 2H), 7.81~7.85(d, 2H), 8.04~8.06 (d, 2H).

[0048]

Embodiment 2

[0050] Add 2.8g (0.02mol) of o-nitrotoluene, 3.1g (0.02mol) of o-nitrobenzaldehyde, and 0.9g (0.0028mol) of tetrabutylammonium bromide into a 100mL four-neck flask, then add 15mL of toluene and stir. And keep the temperature at 30~35℃, add dropwise 1.2g (containing 0.6g, 0.015molNaOH) of 50% NaOH solution for 1h, after the dropwise addition, add 0.4g (0.01mol) of solid sodium hydroxide, and continue the reaction for 5 ~12 hours. The reaction solution was washed with water to neutrality, the organic layer was evaporated toluene under reduced pressure, and finally an appropriate amount of methanol solution was added to precipitate a solid product, which was filtered and dried to obtain 4.4 g of yellow solid 2,2'-dinitrostilbene, yield It is 81.4%, and the purity is more than 98%.

[0051] 1 HNMR (400MHz, CDCl 3 ): 7.46~7.50 (t, 2H), 7.57 (s, 2H), 7.65~7.69(t, 2H), 7.81~7.85(d, 2H), 8.04~8.06 (d, 2H).

[0052]

Embodiment 3

[0054]Add 2.8g (0.02mol) of o-nitrotoluene, 3.1g (0.02mol) of o-nitrobenzaldehyde, and 0.5g (0.00155mol) of tetrabutylammonium bromide into a 100mL four-neck flask, then add 15mL of benzene and stir. And keep the temperature at 30~35°C, add dropwise 1.2g of 50% NaOH solution (containing 0.6g, 0.015molNaOH) for 1h, after the dropwise addition, add 0.2g (0.005mol) of solid sodium hydroxide, and continue the reaction for 5 ~12 hours. The reaction solution was washed with water to neutrality, the organic layer was evaporated with benzene solvent under reduced pressure, and finally an appropriate amount of methanol solution was added to precipitate a solid product, which was filtered, dried, and dried to obtain 4.3 g of yellow solid 2,2'-dinitrostilbene. The rate was 79.6%, and the purity was >96%.

[0055] 1 HNMR (400MHz, CDCl 3 ): 7.46~7.50 (t, 2H), 7.57 (s, 2H), 7.65~7.69(t, 2H), 7.81~7.85(d, 2H), 8.04~8.06 (d, 2H).

[0056]

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Abstract

The invention discloses a synthesis method for 2,2'-dinitryl diphenylethene. The synthesis method comprises the steps as follows: taking o-nitrotoluene and o-nitrobenzaldehyde as starting materials, carrying out one-step condensation reaction on the o-nitrotoluene and the o-nitrobenzaldehyde under the action of a phase transfer catalyst-quaternary ammonium salt and an inorganic strong alkali to obtain the 2,2'-dinitryl diphenylethene. According to the synthesis method for the 2,2'-dinitryl diphenylethene, the yield is about 80%, the bromination process is not used, and the obtained 2,2'-dinitryl diphenylethene contains no bromine residues. The one-step synthesis method for the 2,2'-dinitryl diphenylethene has the advantages of simple and short process flow, simple reaction step, less pollution and high product yield and purity, and can satisfy the requirements of the industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing 2,2'-dinitrostilbene. Background technique [0002] 2,2'-Dinitrostilbene is an important pharmaceutical intermediate and fine chemical product, and its structural formula is shown in Formula 1 below: [0003] [0004] Formula 1 Chemical structure of 2,2'-dinitrostilbene. [0005] According to existing literature reports, the traditional synthetic route of this compound is generally to use o-nitrotoluene as a starting material, then add petroleum ether, sodium methoxide, ethyl formate to first synthesize 2,2'-dinitrobibenzyl, and then After bromination and debromination to form a double bond, the 2,2'-dinitrostilbene product is obtained, and the reaction route is shown in the following formula 2: [0006] [0007] Formula 2 The traditional synthetic route of 2,2'-dinitrostilbene. [0008] The total yield of the product obtained by this synthetic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/06C07C201/12
Inventor 宋国强唐龙王车礼邹振荣钱振青陆惠刚
Owner JIANGSU TOHOPE PHARMA
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