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New synthesizing method for 1,6-(paramidyl phenyl)dihexyl ether

The technology of an amidino phenyl group and a synthesis method, which is applied in 1 field, can solve the problems of small industrial value, pollution, low yield of intermediate B, etc., and achieves the effects of reducing production cost, safe and easy-to-obtain raw materials, and improving total yield

Active Publication Date: 2018-07-20
GUANGZHOU TROJAN PHARMATEC LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the catalyzed reaction of sodium methoxide and acetic acid reported in the literature in the second step of synthesis, the yield of intermediate B is very low, and even the product cannot be obtained, and the industrial value is small; the method that can obtain the expected result at present is still anhydrous hydrogen chloride catalyzed reaction, Then ammonolysis, but there are obvious defects in this method: hydrogen chloride gas is a strong corrosive gas and the amount is large, the pollution is serious during use, the safety is poor, the equipment anti-corrosion requirements are high, and the amount of waste acid is difficult to handle, and the reaction time of alcoholysis Long; use volatile gas ammonia during ammonolysis, serious pollution, poor safety; in a word this method is not suitable for large-scale industrial production

Method used

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  • New synthesizing method for 1,6-(paramidyl phenyl)dihexyl ether
  • New synthesizing method for 1,6-(paramidyl phenyl)dihexyl ether

Examples

Experimental program
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Effect test

Embodiment 1

[0043] A kind of embodiment of the new synthetic method of 1,6-(p-amidinophenyl) hexylene diether of the present invention, comprises the following steps:

[0044] (1) Synthesis of 1,6-(p-cyanophenyl) hexamethylene diether:

[0045] In a 1L four-neck flask equipped with a stirring, thermometer, dropping funnel and reflux condenser, add 500ml of ethanol and 57.16g (0.840mol; 1.5eq) of sodium ethylate in sequence, stir to dissolve, then add 100g (0.840 mol; 1.5eq) p-cyanophenol, then heated up to 60°C and refluxed for 1 hour, then slowly added 136.6g (0.560mol; 1eq) 1,6-dibromohexane dropwise at this temperature, and maintained the temperature after dropping Sampling was carried out after 4 hours of reaction, the reaction was completed by liquid phase monitoring, the temperature was lowered to 20°C, and after stirring for 1 hour, it was filtered to obtain a solid wet product. After beating with 300 ml of water, it was filtered and dried to obtain 121.0 g of a white solid, which ...

Embodiment 2

[0054] A kind of embodiment of the new synthetic method of 1,6-(p-amidinophenyl) hexylene diether of the present invention, comprises the following steps:

[0055] (1) Synthesis of 1,6-(p-cyanophenyl) hexamethylene diether:

[0056] In a 1L four-neck flask equipped with stirring, a thermometer, a dropping funnel, and a reflux condenser, add 500ml of ethanol and 57.16g (0.840mol; 2.2eq) of sodium ethoxide in sequence, stir to dissolve it completely, cool to room temperature, and divide Add 100g (0.840mol; 2.2eq) of p-cyanophenol in batches, then raise the temperature to 80°C and react for 1h, then add 93.2g (0.382mol; 1eq) of 1,6-dibromohexane dropwise under the control of the temperature, and keep React at this temperature for 1 hour and take samples. The liquid phase monitors that the reaction is complete. Cool down to 25°C, stir for 1 hour, and filter it to obtain a solid wet product. After beating with 300ml of water, filter and dry to obtain 116.8g of a white solid, which ...

Embodiment 3

[0066] A kind of embodiment of the new synthetic method of 1,6-(p-amidinophenyl) hexylene diether of the present invention, comprises the following steps:

[0067] (1) Synthesis of 1,6-(p-cyanophenyl)hexylene diether: In a 1L four-neck flask equipped with a stirring, thermometer, dropping funnel and reflux condenser, add 500ml of ethanol and 57.2g (0.840 mol; 2eq) sodium ethylate, stir to dissolve it completely, add 100g (0.840mol; 2eq) of p-cyanophenol in batches, then raise the temperature to 65°C and reflux for 1h, then add 102.5g (0.42mol; 1eq) dropwise under reflux 1,6-dibromohexane, after dripping, keep the reaction at the temperature for 10 hours to take samples, monitor the reaction in liquid phase, cool down to 22°C, stir for 1 hour, filter it to obtain a solid wet product, beat with 300ml of water, filter and dry, 125.2 g of white solid was obtained, which was 1,6-(p-cyanophenyl)hexamethylene ether;

[0068] The yield of 1,6-(p-cyanophenyl)hexamethylene diether in t...

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Abstract

The invention discloses a new synthesizing method for 1,6-(paramidyl phenyl)dihexyl ether. The new synthesizing method for the 1,6-(paramidyl phenyl)dihexyl ether comprises the following steps: (1) enabling cyanophenol and 1,6-dibromohexane to react to obtain 1,6-(p-cyanophenyl)dihexyl ether; (2) enabling the 1,6-(p-cyanophenyl)dihexyl ether obtained in the step (1) to react with hydroxylamine orhydroxylamine hydrochloride in the existence of alkaline to obtain 1,6-(p-amidoxime-phenyl)dihexyl ether; (3) reducing the 1,6-(p-amidoxime-phenyl)dihexyl ether obtained in the step (2) to obtain the1,6-(paramidyl phenyl)dihexyl ether; or enabling the 1,6-(p-amidoxime-phenyl)dihexyl ether to react with an esterifying reagent or an etherifying reagent to obtain an ester or an ether, and then performing a reducing reaction to obtain the 1,6-(paramidyl phenyl)dihexyl ether. The new synthesizing method disclosed by the invention is more environmentally friendly compared with the conventional process; the yield is greatly improved; the new synthesizing method disclosed by the invention is applicable to large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a new synthesis method of 1,6-(p-amidinophenyl)hexamethylene diether. Background technique [0002] 1,6-(p-Amidinophenyl)hexylenediethionate is a new type of water-soluble cationic dandruff and antipruritic agent with broad-spectrum antibacterial and bactericidal properties. Positive bacteria, negative bacteria, and various molds and yeasts have high killing and inhibiting effects, and are very safe and mild, with little irritation to the skin, and excellent compatibility with commonly used raw materials in daily chemical products. has a very important and unique status. [0003] The synthesis of 1,6-(p-amidinophenyl)hexanediethionate generally involves the following three steps: (1) Synthesis of 1 by reacting p-cyanophenol with 1,6-dibromohexane, 6-(p-cyanophenyl)hexamethylene ether (intermediate A), (2) alcoholysis of intermediate 1 to give 1,6-(p-imidop...

Claims

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Application Information

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IPC IPC(8): C07C259/18C07C253/30C07C255/54C07C257/18
CPCC07C253/30C07C257/18C07C259/18C07C255/54
Inventor 郑庆泉
Owner GUANGZHOU TROJAN PHARMATEC LTD
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