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Synthetic method of nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound

A nitrogen heterocyclic compound and a synthesis method technology are applied in the field of synthesis of nitrogen-containing heterocyclic benzonitrile or phthalonitrile compounds, can solve the problems of unsuitability for scale-up production, harsh synthesis conditions, expensive catalysts, etc., and achieve low cost, Easy-to-obtain, mild reaction conditions

Inactive Publication Date: 2015-07-22
LIAOCHENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires that the system must be anhydrous and oxygen-free, so the synthesis conditions are relatively harsh, and the post-treatment is also relatively cumbersome, and because the catalyst is relatively expensive, it is not suitable for scale-up production

Method used

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  • Synthetic method of nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of 4-(1 hydrogen-pyrrol-1-yl) benzonitrile, concrete steps are as follows:

[0027] Add 0.11mol (7.5g) of pyrrole, 0.1mol (12.1g) of 4-fluorobenzonitrile, 0.16mol (22.1g) of potassium carbonate and 100ml of THF into a 250ml round-bottomed flask, replace with nitrogen 3 times, and place in an oil bath The pot was heated to reflux for 5h. Cool to room temperature, pour into 500ml of ice water, filter with suction, and dry in the air. Petroleum ether: ethyl acetate volume ratio = 20:1 was used as the developer to pass through the flash column to obtain 14.3 g of white powder with a yield of 85%. Proton NMR data of the target product: 1 H NMR (CDCl 3 ,400MHz), (TMS,ppm):7.78(m,2H),7.57-7.40(m,2H),7.13(s,1H),6.40(s,2H).

Embodiment 2

[0029] The synthesis of 4-dianiline benzonitrile, concrete steps are as follows:

[0030] Add 55mmol (9.31g) of diphenylamine, 50mmol (6.05g) of 4-fluorobenzonitrile, and 70ml of DMF into a 150ml round bottom flask, lower it to 0°C, and add 75mmol (1.8g) of NaH to the above system in 5 batches In the process, the time interval between each batch is 20min. After the addition, the system is warmed up to 80°C and stirred overnight. The system was cooled to room temperature, then poured into about 250ml of ice water, filtered with suction, and dried in the air. Petroleum ether: ethyl acetate volume ratio = 30:1 was used as the developer to pass through the flash column, and finally the target product was light yellow solid powder, 10.3g, with a yield of 76.3%. Proton NMR data of the target product: 1 H NMR (CDCl 3 ,400MHz), (TMS,ppm):7.42(d,2H),7.34(t,4H),7.16(m,6H),6.96(d,2H).

Embodiment 3

[0032] For the synthesis of 4-(2(4-methoxyphenyl)amino)benzonitrile, the specific steps are the same as in Example 2. Substrate: 14.3mmol (4.72g) bis(4-methoxyphenyl)amine, 13mmol (1.57g) 4-fluorobenzonitrile, 20mmol (0.48g) NaH, DMF 60ml. Petroleum ether: ethyl acetate volume ratio = 30:1 was used as a developer to pass through the column to obtain 3.1 g of white solid powder with a yield of 71.9%. The proton NMR data of the target product are: 1 H NMR (CDCl 3 ,400MHz), (TMS,ppm):7.37(d,2H),7.12(d,4H),6.90(d,4H),6.81(d,2H),3.83(s,6H).

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Abstract

The invention provides a synthetic method of a nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound. The method comprises steps as follows: 4-fluorobenzonitrile or 4-fluorophthalonitrile is taken as a raw material and has a heating reaction with nitrogen heterocyclic and alkali in DMF (dimethyl formamide) or THF (tetrahydrofuran) under the reaction condition of 60 DEGC-120 DEG C for 5-10 h, and a target product is obtained. The synthetic method has the advantages as follows: (1), compared with the prior art, the synthetic method has mild reaction conditions, aftertreatment is simple and easy to operate, the obtained target product is easy to purify, and the yield is higher; (2), reaction raw materials are low in cost and easy to obtain, and the nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound is suitable for large-scale production and more easily has an electrophilic reaction with N by comparison with conventional iodine, bromine or chlorine under the alkaline condition; (3), with adoption of the method for synthesizing the nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound, the cost is remarkably reduced, and the method can be popularized and applied to industrial production.

Description

technical field [0001] The invention belongs to the field of synthetic chemistry, and in particular relates to a synthesis method of a nitrogen-containing heterocyclic benzonitrile or phthalonitrile compound. Background technique [0002] As an important organic intermediate, benzonitrile derivatives or phthalonitrile derivatives not only play an important role in medical treatment, pesticides, antioxidants and dyes, but also show relatively high performance in photoelectric materials that have emerged in recent years. great practical value. Benzonitrile derivatives can be used as precursors for the synthesis of dye DPP (diketopyrrolopyrrole), and also as important intermediates for the synthesis of oxazine or azole derivatives. The main application of phthalonitrile derivatives in photoelectric materials is the synthesis of substituted phthalocyanines. [0003] At present, the synthetic method of nitrogen-containing heterocyclic benzonitrile or phthalonitrile compound is ...

Claims

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Application Information

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IPC IPC(8): C07D207/327C07D233/56C07D249/08C07D209/86C07D231/12C07C253/30C07C255/58C07D279/22
CPCC07D207/327C07C253/30C07D209/86C07D231/12C07D233/56C07D249/08C07D279/22C07C255/58
Inventor 泮廷廷孙元伟姜国山罗佩佩王素娜张宪玺杜玉昌
Owner LIAOCHENG UNIV
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