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Method for synthesizing dicyano diarylethene compound

A technology of dicyanodiarylethene and synthesis method, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, can solve problems such as restricting industrialization, and achieves reduction of reaction cost, pollution, and reaction bottom. Broad spectrum effect

Active Publication Date: 2018-06-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

All there are some deficiencies in the above synthetic methods of these dicyanodiarylethene compounds, restricting its possibility of becoming industrialized

Method used

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  • Method for synthesizing dicyano diarylethene compound
  • Method for synthesizing dicyano diarylethene compound
  • Method for synthesizing dicyano diarylethene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of dicyano-stilbene (II-1)

[0025] The reaction formula is as follows:

[0026]

[0027] Under air atmosphere, add 0.1g (Ru molar mass is 5‰ of (I-1)) Ru / C catalyst, 15mmol K 2 CO 3 Into the reaction flask, add 50mL o-dichlorobenzene, then add 1.172g (10mmol) phenylacetonitrile (I-1) into the reaction flask under stirring, keep the temperature at about 160°C, stir for 30 hours, TLC Monitor until the basic reaction of raw material (I-1) is complete. After the reaction, add 20mL water to the reaction solution, stir and filter once to obtain a filter cake and a filtrate, wash the filter cake once with 5mL of o-dichlorobenzene and then filter it twice, and recycle the filter cake twice to obtain Ru / C catalyst; combine the primary filtrate and the secondary filtrate, collect the organic phase after standing for stratification, and reclaim o-dichlorobenzene through distillation under reduced pressure under 10mmHg (collecting the fraction ...

Embodiment 2

[0029] Embodiment 2: the preparation of dicyano two p-chlorostyrene (II-2)

[0030] The reaction formula is as follows:

[0031]

[0032] Under air atmosphere, add 0.1g (Ru molar mass is 5‰ of (I-1)) Ru / C catalyst, 15mmol K 2 CO 3 Add 50mL o-dichlorobenzene to the reaction flask, then add 1.516g (10mmol) p-chlorophenylacetonitrile (I-2) into the reaction flask under stirring, keep the temperature at about 160°C, and stir for 30 hours , the following operations were the same as in Example 1, and finally 1.406 g of the dicyanodi-p-chlorostyrene compound shown in formula (II-2) was obtained, with a yield of 94% and a GC-MS purity of 99.0%. The structural representation of compound formula (II-2) is as follows:

[0033] 1 H-NMR (CDCl 3 ): δ7.73(d, 2H, J=6Hz), 7.51(d, 2H, J=12Hz), 7.35-7.32(m, 4H); IRν max (cm -1):3092,2224,1592,1492,1404,1257,1093,1012,826,824; GC-MS(EI):m / z 298[M + ]

Embodiment 3

[0034] Embodiment 3: the preparation of dicyano two-trifluoromethylstyrene (II-3)

[0035] The reaction formula is as follows:

[0036]

[0037] Under air atmosphere, add 0.1g (Ru molar mass is 5‰ of (I-1)) Ru / C catalyst, 15mmol K 2 CO 3 In the reaction flask, add 50mL o-dichlorobenzene, then add 1.852g (10mmol) m-trifluoromethylphenylacetonitrile (I-3) into the reaction flask under stirring, keep the temperature at about 160°C, stir After reacting for 35 hours, the following operations were the same as those in Example 1. Finally, 1.593 g of the dicyanodi-trifluoromethylstyrene compound represented by formula (II-3) was obtained, with a yield of 87% and a GC-MS purity of 99.0%. The structural representation of compound formula (II-3) is as follows:

[0038] 1 H-NMR (CDCl 3 ):δ8.12(s,2H),7.92(m,2H),7.69(m,2H),7.54(m,2H); 13 C-NMR (CDCl 3 ): δ141.58, 133.41, 132.03, 130.23, 129.21, 125.54, 124.12, 122.15, 115.68; IRν max (cm -1 ):2226,1333,1171,1132,803,697; GC-MS(E...

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Abstract

The invention discloses a method for synthesizing a dicyano diarylethene compound. The method includes: in an air atmosphere, taking substituted phenylacetonitrile as a raw material, taking Ru / C and K2CO3 as catalysts, in o-dichlorobenzene, after the reaction is completed at 140-160 DEG C, separating and purifying the reaction solution, and obtaining the dicyano diarylethene compound. The Ru / C catalyst used in the method not only is inexpensive and easily available, but also is a heterogeneous catalytic system in the reaction. Therefore, the catalyst and a solvent are very convenient to recycle, and can be repeatedly applied. The reaction materials are various and cheap and suitable for synthesizing various substituted dicyano diarylethene compounds. The post-treatment is simple, the product purity is good, and the yield is good.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing dicyanodiarylethene compounds. (2) Background technology [0002] Acrylonitrile compounds are important intermediates in organic synthesis. Acrylonitrile compounds exist in nature and in all aspects of human life, and are the basic framework and important constituent units of many natural products and medicines. In particular, the dicyanodiarylethene compound is extremely widely used, such as it can be used in chemical industry, medicine, materials and other industries, so its synthetic method has always attracted people's attention. Utilize iodine and sodium alkoxide to synthesize dicyano-stilbene compounds such as Hsiu-Chih Yeh, need to use low temperature, flammable and explosive solvent ether in the synthetic process of this type of method, post-processing trouble, and catalyst can't recycle (Hsiu-Chih Yeh et al., J. Org. Chem. 2004, 69, 6455-6462). Elison et al. have synthesized dicyanodiar...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/34C07C255/35C07C255/37
CPCC07C253/30C07C255/34C07C255/35C07C255/37
Inventor 王宇光朱冰春张程
Owner ZHEJIANG UNIV OF TECH
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