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Synthesis method for aryl azide compound

A synthetic method, the technology of aryl azide, which is applied in the field of synthesis of azide compounds, can solve the problems of harsh conditions, small scope of application, low yield, etc., and achieve the effects of mild reaction conditions, wide selection range, and simple raw materials

Inactive Publication Date: 2017-04-26
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still many defects in the above method, such as high pH requirements during diazotization, difficult control, high toxicity of raw materials, easy generation of by-products, low yield, small scope of application, large limitations, and harsh conditions. Therefore, its further application is limited

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  • Synthesis method for aryl azide compound
  • Synthesis method for aryl azide compound
  • Synthesis method for aryl azide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Using different copper salts as catalysts, 1.0mmol iodobenzene, 1.2mmol sodium azide, 0.2mmol DBU and 0.1mmol catalyst were sequentially added to a reaction flask containing 3.0mL dimethyl sulfoxide, and the reaction mixture was heated at 95 Stir the reaction at ℃, track the reaction until the reaction is complete by TLC, add a few drops of ammonia water to the reaction mixture, then extract with ethyl acetate (10mL×3), wash with saturated brine once, dry, filter with suction, spin off the solvent, and The target product was obtained through chromatographic purification, and the influence of different catalysts on the reaction yield is shown in Table 1.

[0010] Table 1 Effect of different catalysts on reaction yield

[0011] Group catalyst Reaction time (h) Yield (%) 1 Cu(OAc) 2 ·H 2 o

Embodiment 2

[0013] Add 1.0mmol of iodobenzene, 1.2mmol of sodium azide, 0.2mmol of DBU and 0.1mmol of copper acetate to a reaction flask containing 3.0mL of solvent in sequence, and stir the reaction mixture at 95°C for a reaction, followed by TLC until the reaction is complete. Add a few drops of ammonia water to the reaction mixture, then extract with ethyl acetate (10mL×3), wash once with saturated brine, dry, filter with suction, spin off the solvent, and purify by column chromatography to obtain the target product. The impact of the yield is shown in Table 2.

[0014] Table 2 Effect of different solvents on the reaction yield

[0015] Group solvent Reaction time (h) Yield (%) 1 DMSO 1.5 93 2 DMF 5.0 80 3 MeOH 8.0 45 4 EtOH 8.0 40 5 h 2 o

Embodiment 3

[0017]

[0018] Add 1.0mmol of iodobenzene, 1.2mmol of sodium azide, 0.15mmol of DBU and 0.1mmol of copper acetate to a reaction flask containing 3mL of dimethyl sulfoxide, and stir the reaction mixture at 95°C for 1.5h, followed by TLC. After the reaction is complete, add a few drops of ammonia water to the reaction mixture, then extract with ethyl acetate (10mL×3), wash once with saturated brine, dry, filter with suction, spin off the solvent, and purify by column chromatography to obtain the target product , yield 92%.

[0019] Data characterization of phenyl azide: pale yellow liquid; 1 H NMR (400 MHz, CDCl 3 ) δ: 7.38-7.34 (m,2H), 7.15 (t, J = 8.0 Hz, 1H), 7.04 (d, J = 8.0 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ: 140.0, 129.8, 124.9, 119.0.

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Abstract

The invention discloses a synthesis method for an aryl azide compound. The synthesis method includes the steps of: adding an iodo-aryl compound, sodium azide, 1,8-diazabicyclo[5.4.0]undecane-7-ene and a catalyst into a reaction container filled with a solvent, performing a stirring reaction to the reaction mixture at 60-105 DEG C with TLC tracing detection until the reaction is completed, adding ammonia water to the reaction mixture, extracting the reaction mixture for 3 times by ethyl acetate, washing the reaction mixture for 1 time by saturated salt water, drying an organic phase, performing suction filtration and spinning solvent removal, and performing column chromatographic purification to obtain a target product. The method employs easy-to-obtained raw materials and has wide selection range of copper source of the catalyst, has mild reaction condition, simple operation and high yield.

Description

technical field [0001] The invention belongs to the technical field of synthesis of azide compounds, and in particular relates to a synthesis method of aryl azide compounds. Background technique [0002] Aryl azide compounds contain azido-based high-energy active functional groups, which are an important class of chemical synthesis intermediates and are widely used in many fields such as organic synthesis, chemical biology, functional materials, and clinical medicine. In addition, with the introduction of azido groups, conversion reactions of some important functional groups can also be realized, such as the famous "Click" reaction and Staudinger reaction. In recent years, with the comprehensive understanding of the properties of azide and the improvement of experimental safety technology, this type of compound has regained the attention of researchers, especially at the beginning of this century, Sharpless et al. -Since the development of dipolar cycloaddition into a "clic...

Claims

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Application Information

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IPC IPC(8): C07C247/16
CPCC07C247/16
Inventor 姜玉钦赵亚茹马素好李兴丰董文佩徐桂清
Owner HENAN NORMAL UNIV
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