Aryl triazene compound preparation method

A technology for aryl triazene and compound, which is applied in the field of preparation of aryl triazene compounds, namely 1--3-triaza-1-ene, can solve the problems of difficulty in recovery, expensive catalyst and the like, and achieves a high price. Inexpensive, mild reaction conditions

Pending Publication Date: 2019-12-20
ZHEJIANG UNIV OF TECH
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are many preparation methods for triazene compounds. For example, in 2010, Nahkai, A. et al. reported the reaction of aryl azides with Grignard reagents to generate triazene in a stable configuration through 1,3 proton transfer. Compound; in 2011, Wang Yang et al. added a certain amount of concentrated hydrochloric acid to the ethanol solution of amine compounds, fully protonated at room temperature, and then slowly added an aqueous solution of sodium nitrite dropwise at -10°C until the diazotization reaction was complete. Add ethanol solution of secondary amine and sodium carbonate solid, react for a period of time to obtain triazene compounds; aryl azide reacts with Grignard reagent or organolithium reagent to prepare aryl triazene and other methods, but there are certain problems , such as catalysts are expensive, difficult to recycle, etc.

Method used

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  • Aryl triazene compound preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1 (the influence of diazotization process temperature on yield)

[0024] Add 1.36g (0.01mmol) of 3,4-dichloroaniline and 1mL of distilled water into a 50mL flask, heat to 75°C, add 5.5mL of concentrated hydrochloric acid with a mass fraction of 36% dropwise after it dissolves, add 5mL of distilled water after stirring vigorously, Heat and stir intermittently until it is completely dissolved, add 15mL of water after natural cooling to room temperature, stir to form a uniform white milky suspension, place the flask in an ice-water bath at -5 to 5°C, and add sodium nitrite aqueous solution dropwise (5 mL, 0.0105 mol, 2.1 M), and continued to stir for 2 h to obtain an aqueous solution of 3,4-dichloroaniline diazonium salt.

[0025] Add aqueous sodium hydroxide solution (15mL, 0.06mol, 4M) into a 100mL beaker, bathe in ice water, and when the solution drops to -5~5°C, slowly add 3,4-dichloroaniline dropwise within 30min under vigorous stirring For the diazonium s...

Embodiment 2

[0032] Embodiment 2 (the influence of the mol ratio of substituted aniline and sodium nitrite on productive rate)

[0033] Add 1.36g (0.01mol) of 3,4-dichloroaniline and 1mL of distilled water into a 50mL flask, heat to 75°C, and after it dissolves, add 5.5mL of concentrated hydrochloric acid with a mass fraction of 36%, add 5mL of distilled water after vigorous stirring , heated and stirred intermittently until it was completely dissolved, cooled naturally to room temperature, added 15 mL of water, stirred to form a uniform white milky suspension, placed the flask in an ice-water bath at 0-5°C, repeated the above experiment three times, and Add dropwise 5.0mL, 5.7mL, 6.2mL of 2.1M sodium nitrite aqueous solution (that is, the amount of sodium nitrite is 0.0105, 0.012, 0.013mol respectively), and continue to stir for 2h to obtain three parts of 3,4-di Chloroaniline diazonium salt solution, and coded as a, b, c;

[0034] Take three 100mL beakers and add aqueous sodium hydroxid...

Embodiment 3

[0042] Embodiment 3 (the influence of reactant (Ⅲ) preheating temperature on yield)

[0043]Add 1.36g (0.01mmol) of 3,4-dichloroaniline and 1mL of distilled water into a 50mL flask, heat to 75°C, add 5.5mL of concentrated hydrochloric acid with a mass fraction of 36% dropwise after it dissolves, add 5mL of distilled water after stirring vigorously, Heat and stir intermittently until it dissolves completely, add 15mL of water after natural cooling to room temperature, stir to form a uniform white milky suspension, place the flask in an ice-water bath at 0-5°C, add sodium nitrite aqueous solution ( 5mL, 0.0105mol, 2.1M), and continued stirring for 2h to obtain an aqueous solution of 3,4-dichloroaniline diazonium salt.

[0044] Add aqueous sodium hydroxide solution (15mL, 0.06mol, 4M) into a 100mL beaker, take an ice-water bath, and when the solution drops to 0-5°C, slowly add 3,4-dichloroaniline weight dropwise within 30min under vigorous stirring. Nitrogen salt solution, after...

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Abstract

The invention discloses an aryl triazene compound preparation method, and belongs to the technical field of organic synthesis, wherein the aryl triazene compound is 1-(3,4-dichlorophenyl)-3-(4-fluorophenyl)triazo-1-ene. The preparation method comprises: diazotizing a substituted aniline raw material under the action of sodium nitrite under an acidic condition, adding another substituted aniline under an alkaline condition, carrying out a reaction, carrying out TLC monitoring until the reaction is finished, and separating and purifying the reaction solution to obtain the aryl triazene compound.According to the present invention, by using the technical scheme, the new method for synthesizing 1-(3,4-dichlorophenyl)-3-(4-fluorophenyl)triazo-1-ene by using inexpensive and easily available substituted aniline as a raw material has characteristics of mild reaction condition, low raw material price and good industrial prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to the preparation of 1-(3,4-dichlorophenyl)-3-(4-fluorophenyl)triazene-1-ene, an aryl triazene compound method. Background technique [0002] Triazene refers to an organic compound containing three nitrogen atom structural units -N=N-N- in the molecule, and is also called a diazoamino compound. In the molecular structure of this type of compound, three nitrogen atoms are conjugated to each other, thus exhibiting unique physical and chemical properties. The research on triazene can be traced back to the 19th century when Griess first reported the synthesis of triazene in 1862. Since then, this type of compound has gradually been widely used in industries such as medicine, dyes, and food additives. [0003] Aryltriazenes are widely used in protecting groups for natural product synthesis, combinatorial chemistry, synthesis of polymers and oligomers, synthesis of heterocycl...

Claims

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Application Information

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IPC IPC(8): C07C245/24
CPCC07C245/24
Inventor 谭成侠马天扬杨森陈澍邹文倩陶敏
Owner ZHEJIANG UNIV OF TECH
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