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Synthesis method of alkenyl dinitrile compounds

A synthesis method and compound technology are applied in the field of synthesis of enedionitrile compounds, which can solve problems such as a large amount of alkaline waste water, polluted environment and the like, and achieve the effects of high yield, reduced pollution and good purity

Active Publication Date: 2018-08-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional synthesis method of arylene dinitriles is formed by condensation and dehydration of aldehydes and malononitrile under alkaline conditions. The disadvantage of this method is that an equivalent amount of alkali is used, and a large amount of Alkaline wastewater, seriously polluted environment

Method used

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  • Synthesis method of alkenyl dinitrile compounds
  • Synthesis method of alkenyl dinitrile compounds
  • Synthesis method of alkenyl dinitrile compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of enedionitrile compound (III-1)

[0032] The reaction formula is as follows:

[0033]

[0034] Add 5.306g (50mmol) of benzaldehyde (I-1), 0.5g (Ru molar amount is 5‰ of (I-1)) Ru / C catalyst, 3.303g (50mmol) of malononitrile ( II) With 100 mL of ethanol, the reaction was stirred at room temperature for 12 hours. GC-MS detected that the raw material had reacted completely, and the reaction was stopped. The reaction solution was filtered once to obtain the first filtrate and the first filter cake. The first filtrate was used to recover ethanol by the rotary evaporator; the first filter cake was dissolved with 50 mL of dichloromethane, and the second filter was filtered to obtain the second filtrate and the second filter cake, using 5 mL The second filter cake was washed with dichloromethane and filtered three times to obtain the third filtrate and the third filter cake. The third filter cake is the Ru / C catalyst and can be used in the next batch of rea...

Embodiment 2

[0036] Example 2: Preparation of enedionitrile compound (III-2)

[0037] The reaction formula is as follows:

[0038]

[0039] Add 6.008g (50mmol) o-methylbenzaldehyde (I-2), 0.5g (Ru molar amount is 5‰ of (I-2)) Ru / C catalyst, 3.303g (50mmol) propylene The dinitrile (II) and 100 mL of ethanol were stirred at room temperature for 14 hours, and the following operations were the same as in Example 1. Finally, 8.242 g of solid was obtained, the yield was 98.0%, and the GC-MS purity was 99.0%. The structure of compound formula (III-2) is characterized as follows:

[0040] 1 H-NMR(CDCl 3 ,500MHz):δ8.12(s,1H),8.11-8.09(m,1H),7.38-7.33(m,2H),2.46(s,3H); 13 C-NMR(CDCl 3 ,125MHz):δ158.2,139.8,134.3,131.5,130.0,128.4,127.1,113.9,112.5,84.1,19.9; GC-MS(EI): m / z 168[M + ].

Embodiment 3

[0041] Example 3: Preparation of enedionitrile compound (III-3)

[0042] The reaction formula is as follows:

[0043]

[0044] Add 6.008g (50mmol) of p-methylbenzaldehyde (I-3), 0.5g (Ru molar amount is 5‰ of (I-3)) Ru / C catalyst, 3.303g (50mmol) of propylene into the reaction flask Dinitrile II and 80 mL of ethanol were stirred at room temperature for 10 hours, and the following operations were the same as in Example 1. Finally, 8.326 g of solid was obtained, the yield was 99.0%, and the GC-MS purity was 99.0%. The structure of compound formula (III-3) is characterized as follows:

[0045] 1 H-NMR(CDCl 3 ,500MHz): δ8.20(d,J=8.1Hz,2H), 7.73(s,1H), 7.35(d,J=8.1Hz,2H), 2.47(s,3H); 13 C-NMR(CDCl 3 ,125MHz):δ159.8,146.4,130.9,130.4,128.4,114.0,112.9,81.1,22.0; GC-MS(EI): m / z 168[M + ].

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Abstract

The invention discloses a synthesis method of alkenyl dinitrile compounds. The preparation method comprises the following steps: taking substituted aldehyde and malononitrile as raw materials, takingRu / C as a catalyst, carrying out a reaction at 20-60 DEG C in ethanol, and carrying out separation and purification on the reaction liquid after the reaction to obtain an alkenyl dinitrile compound. The Ru / C catalyst used in the synthesis method is cheap and is easy to obtain; the Ru / C catalyst is a heterogeneous catalytic system in the reaction, so that the catalyst and a solvent are very convenient to recycle and can be repeatedly used; the reaction raw materials are diverse and cheap, are easily available, and are suitable for the synthesis of various substituted alkenyl dinitrile compounds. The post-treatment is simple, the product purity is good, and the yield is high.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing enedionitriles. (2) Background technology [0002] Dinitrile compounds are an important class of bulk chemical intermediates, which are widely used in chemical, materials, medicine, pesticide and other industries. For example, NK1 receptor antagonists have good effects in the treatment of depression, and they can be used in the treatment of tumors; and enedionitriles can be used to synthesize NK1 receptor ligands (Recio R et al., European Journal of Medicinal Chemistry, 2017, 138,644-660.). Hassaneen, Hamdi M. et al. reported that a condensed ring compound with antibacterial activity can be synthesized from ene dinitrile compounds (Journal of Heterocyclic Chemistry, 2017, 54(5), 2850-2858.). [0003] The traditional synthetic method of arylene dinitrile compounds is formed by condensation and dehydration of aldehyde and malononitrile under alkaline conditions. The disadvantage of this method is that equ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/34C07C255/35C07C255/37C07C255/09C07D333/24C07B37/00
CPCC07B37/00C07C253/30C07C255/34C07C255/35C07C255/37C07C255/09C07D333/24Y02P20/584
Inventor 王宇光胡芬张程
Owner ZHEJIANG UNIV OF TECH
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