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
View PDF6 Cites 5 Cited by
  • 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

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound
  • Synthetic method of nitrogen heterocyclic ring cyanophenyl or phthalonitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0025] Example 1

[0026] The specific steps for the synthesis of 4-(1hydro-pyrrol-1-yl)benzonitrile are as follows:

[0027] Add 0.11mol (7.5g) pyrrole, 0.1mol (12.1g) 4-fluorobenzonitrile, 0.16mol (22.1g) potassium carbonate and 100ml THF into a 250ml round bottom flask, replace with nitrogen 3 times, and place it in an oil bath Heat the pot to reflux for 5h. Cool to room temperature, pour into 500ml ice water, filter with suction, and dry. The volume ratio of petroleum ether: ethyl acetate=20:1 was used as the developing agent and passed through the fast column to obtain 14.3 g of white powder with a yield of 85%. Hydrogen 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).

Example Embodiment

[0028] Example 2

[0029] The specific steps of the synthesis of 4-diphenylaminobenzonitrile are as follows:

[0030] Add 55mmol (9.31g) diphenylamine, 50mmol (6.05g) 4-fluorobenzonitrile, and 70ml DMF into a 150ml round bottom flask, reduce to 0℃, add 75mmol (1.8g) NaH to the above system in 5 batches The interval between each batch is 20min. After the addition, the system is heated 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. The volume ratio of petroleum ether: ethyl acetate = 30:1 was used as the developing agent to pass the fast column, and the final target product was light yellow solid powder, 10.3 g, and the yield was 76.3%. Hydrogen 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).

Example Embodiment

[0031] Example 3

[0032] For the synthesis of 4-(2(4-methoxyphenyl)amino)benzonitrile, the specific steps are the same as in Example 2. The substrate is: 14.3mmol (4.72g) bis(4-methoxyphenyl)amine, 13mmol (1.57g) 4-fluorobenzonitrile, 20mmol (0.48g) NaH, DMF 60ml. The volume ratio of petroleum ether: ethyl acetate = 30:1 was used as the developing agent and passed through the column to obtain 3.1 g of white solid powder with a yield of 71.9%. The hydrogen nuclear magnetic data of the target product is: 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).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap