Method for synthesizing o-amino diaryl ether and o-amino diaryl sulfur ether

A technology of o-amino diaryl sulfide and o-amino diaryl ether, which is applied in chemical instruments and methods, formation/introduction of amino groups, preparation of amino hydroxy compounds, etc. problem, to achieve the effect of direct reaction, simple method and good activity

Inactive Publication Date: 2013-01-02
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The currently disclosed synthetic method has the disadvantages of poor selectivity, many wastes and narrow scope of application. Before the present inv

Method used

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  • Method for synthesizing o-amino diaryl ether and o-amino diaryl sulfur ether
  • Method for synthesizing o-amino diaryl ether and o-amino diaryl sulfur ether
  • Method for synthesizing o-amino diaryl ether and o-amino diaryl sulfur ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Compound 1: Add metal copper powder (0.05mmol), cesium carbonate (1.0mmol) and polyethylene glycol-600 (2.0g) into a 25mL reaction flask, fill with nitrogen protection, add benzothiazole (0.5mmol) and iodobenzene (1.0 mmol). The reaction mixture was at 140 o Reaction at C until the reaction of the raw materials is complete. After cooling to room temperature, the solvent was evaporated under reduced pressure and separated by column chromatography (petroleum ether: diethyl ether: triethylamine = 30: 1: 1) to obtain a pale yellow liquid. Yield 96%.

Embodiment 2

[0041] Compound 2: Add metal copper powder (0.05mmol), cesium carbonate (1.0mmol) and polyethylene glycol-600 (2.0g) into a 25mL reaction flask, fill with nitrogen protection, add benzothiazole (0.5mmol) and o-iodine Toluene (1.0 mmol). The reaction mixture was at 140 o Reaction at C until the reaction of the raw materials is complete. After cooling to room temperature, the solvent was evaporated under reduced pressure and separated by column chromatography (petroleum ether: diethyl ether: triethylamine = 30: 1: 1) to obtain a pale yellow liquid. Yield 94%.

Embodiment 3

[0043] Compound 3: Add metal copper powder (0.05mmol), sodium carbonate (1.0mmol) and polyethylene glycol-400 (2.0g) to a 25mL reaction flask, fill with nitrogen protection, add benzothiazole (0.5mmol) and p-iodine Aniline (1.0 mmol). The reaction mixture was at 140 o Reaction at C until the reaction of the raw materials is complete. After cooling to room temperature, the solvent was evaporated under reduced pressure and separated by column chromatography (petroleum ether: diethyl ether: triethylamine = 30: 1: 1) to obtain a pale yellow liquid. Yield 93%.

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Abstract

The invention discloses a method for synthesizing o-amino diaryl ether and o-amino diaryl sulfur ether. The method comprises the steps of: adding an iron and/ or copper catalyst in solvent alcohol or water under the action of alkali, and carrying out open loop coupling reaction on catalytic aryl halide and benzoazole compound to prepare the o-amino diaryl ether or o-amino diaryl sulfur ether, wherein the reaction general formula is shown in the specification. The method for preparing the o-amino diaryl ether and o-amino diaryl sulfur ether by the coupling reaction is low in catalyst price, low in toxicity, direct to react, high in atom economy, wide and stable in substrate source and wide in application scope. Under the optimized reaction conditions, the separation yield of target products reaches up to 96%.

Description

technical field [0001] The invention relates to a method for synthesizing o-amino diaryl ether and o-amino diaryl sulfide. Background technique [0002] O-aminodiaryl ethers and o-aminodiaryl sulfides are important organic intermediates that are widely used in the fields of biology and medicine, exhibiting unique anti-inflammatory, anti-tumor, anti-infection, antipsychotic and antidepressant properties. Methods for synthesizing such substances have attracted extensive attention and some progress has been made. [0003] The most common and direct method for the synthesis of o-aminodiaryl ethers and o-aminodiaryl sulfides is the coupling reaction of transition metal-catalyzed carbon-oxygen and carbon-sulfur bond formation, but the initial The reactants are o-aminophenol and o-aminothiophenol, which are difficult to prepare and easy to oxidize, meanwhile, the existence of various active functional groups causes the problem of reaction selectivity. In order to avoid these prob...

Claims

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Application Information

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IPC IPC(8): C07B43/04C07C319/20C07C323/37C07D213/70C07C213/02C07C217/90C07D317/64C07D213/73
Inventor 韩维姚利芳
Owner NANJING NORMAL UNIVERSITY
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