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Method for synthesizing alkoxy aromatic amidine compounds

A technology of alkoxy aromatic amidines and alkoxy aromatic amidines hydrochloride, which is applied in the field of synthesis of aromatic amidines, can solve the problems of cumbersome post-processing operations, large losses, and difficulties in solvent recovery, and saves the intermediate treatment process , Improve product yield and reduce solvent loss

Active Publication Date: 2009-07-15
南京枫华投资管理有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0040] The present invention provides a kind of synthetic method of alkoxy aromatic amidine compound, can overcome the existing synthetic method existing different technological steps to carry out in different reactors, aftertreatment The operation is cumbersome, and there are many types of solvents used, the solvent recovery is difficult and the loss is large. By using the same solvent as the medium, the steps of etherification, imidate esterification, amination and neutralization are combined in a single reaction kettle. , eliminating the cumbersome intermediate treatment process, increasing product yield and reducing production costs

Method used

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  • Method for synthesizing alkoxy aromatic amidine compounds
  • Method for synthesizing alkoxy aromatic amidine compounds
  • Method for synthesizing alkoxy aromatic amidine compounds

Examples

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Embodiment 1

[0065] Dissolve 24g of sodium metal in 500mL of anhydrous methanol, after cooling slightly, add 32g of p-cyanophenol and 76.9mL of dibromohexane, heat to reflux for 16h, cool to 0°C, and pass dry hydrogen chloride gas into the reaction solution to saturation , close the reactor, control the temperature at 30-40°C, react for 3 days, pass dry nitrogen gas, until the acid gas is less, cool to 0°C, pass dry ammonia gas, heat to 60°C, react for 6h , cooled to room temperature, suction filtered, the filter cake was added to water, stirred to form a suspension, solid potassium carbonate was added, stirred for 30 min, suction filtered, washed with water, and dried to obtain 28.5 g of a white powdery solid.

Embodiment 2

[0067] The operation was the same as in Example 1, and the solvent was absolute ethanol to obtain 29.6 g of white powdery solid.

Embodiment 3

[0069] The operation is the same as that in Example 2, and the ammonia gas is changed to add 50 mL of methylamino alcohol solution (30%), heated to 60 ° C, reacted for 4 hours, cooled to room temperature, filtered with suction, the filter cake is added to water, stirred into a suspension, and solid carbonic acid is added Potassium, stirred for 30 minutes, suction filtered, washed with water, and dried to obtain 26.7 g of white powdery solid.

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Abstract

The invention discloses a method for synthesizing alkoxy aryl amidine compound, comprising the following steps: taking cyano-group phenol and alkylogen as raw materials, obtaining alkylphenyl ether by Williamson condensation, directly introducing chlorine hydride gas into the same reaction kettle to generate imidic acid ester hydrochloride, introducing inert gases to drive the chlorine hydride gas out, adding alkaline air or organic amine to prepare amidine hydrochloride by amination and adding alkali to remove chlorine hydride to obtain the target compound. In the method, identical solvent is used as medium and steps of condensation, addition, amination and the like are combined to one step in a single reaction kettle, so that complex intermediate treatment process is excluded and process is simplified; and meanwhile, loss of the solvent can be reduced and yield of product is improved.

Description

technical field [0001] The invention relates to a synthesis method of aromatic amidine compounds, in particular to a synthesis method of alkoxy aromatic amidine compounds. Background technique [0002] Aromatic amidine compounds, such as aromatic diamidine compounds propaneamidine, butaneamidine, pentaneamidine, hexaneamidine and octaneamidine, etc., can be widely used in pesticides, medicine and chemical industry, and can also be used to synthesize nitrogen heterocyclic compounds. Cyclic amidines have good catalytic activity and are curing agents for epoxy resins and polyurethanes. [0003] There are many synthetic methods of aromatic amidines, which can generally be summarized as follows: [0004] 1. The cyano compound is added to ethanol under the catalysis of the base, and ammonium chloride is added to ammonify to generate the base compound, and then the salt is converted into the target compound. Although this method is simple to operate, the yield is very low, and the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/18
Inventor 史鲁秋薛虹宇李华山
Owner 南京枫华投资管理有限公司
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