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Method for synthesizing N-aryl ketoimine by acidic catalytic dehydration

A technology of aryl ketimine and acid catalysis, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of cumbersome post-processing, low yield, unsuitable for large-scale preparation, etc., and achieve product The effect of high yield, high conversion rate of raw materials and short reaction time

Inactive Publication Date: 2013-01-30
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

), such as dehydration in the presence of tetra(ethoxy)titanium, titanium tetrachloride, etc., the post-treatment is cumbersome and the yield is low, so it is not suitable for large-scale preparation

Method used

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  • Method for synthesizing N-aryl ketoimine by acidic catalytic dehydration
  • Method for synthesizing N-aryl ketoimine by acidic catalytic dehydration
  • Method for synthesizing N-aryl ketoimine by acidic catalytic dehydration

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of immobilized perchloric acid

[0025] Stir 25.0 g of silica gel (200-400 mesh) and 2.0 g of 70% perchloric acid aqueous solution in 50 mL of ether for 1 hour, concentrate and dry at 100°C for 24 hours under vacuum to obtain 26.2 g of white powder. The acid equivalent is: 0.53±0.02 meq / g.

Embodiment 2

[0026] Embodiment 2: the preparation of immobilized sulfuric acid

[0027] Within 30 minutes, drop 19.4 grams of chlorosulfonic acid into 50.0 grams of dry silica gel (200-400 mesh), shake for 30 minutes after dropping, wash with water and dry at 100°C for 24 hours under vacuum to obtain 61.5 grams of white powder . The acid equivalent is: 2.51±0.02 meq / g.

Embodiment 3

[0028] Embodiment 3: the preparation of immobilized benzenesulfonic acid

[0029] In a 500mL reaction bottle, add 5g of activated carbon, 43g of 4-diazobenzenesulfonic acid aqueous solution and 100mL of ethanol, place the reaction system in an ice-water bath and stir, and keep the temperature in the bottle at 0-5°C within 30 minutes. 250 mL of 50% H 3 PO 2 The aqueous solution continued to stir for 1 hour after dripping, filtered, washed with water, washed with acetone, and dried at 100° C. under vacuum for 24 hours to obtain 23.0 grams of black powder. The acid equivalent is: 4.99±0.02 meq / g.

[0030] In the following examples, unless there is a special statement, the order of adding the reaction materials can be freely combined among the materials. In the embodiment, 2-methyl-6-ethylaniline (content 97%) and methoxyacetone (content 96%) are used as raw materials to prepare the product 2-methyl-6-ethyl-N-(2-methyl Oxygen-1-methylethylene)aniline (imine for short) is mainl...

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Abstract

The invention discloses a method for synthesizing N-aryl ketoimine by acidic catalytic dehydration, characterized by using inorganic acid or solid acid as a catalyst, in the presence of azeotropic desiccant, conducting heating reflux reaction, and condensing ketone and arylamine to obtain N-aryl ketoimine. According to the invention, the method has the advantages of simple operation, high raw material conversion rate, good reaction selectivity, high product yield, good product quality, and easiness in realizing continuous operation, and is suitable for large scale preparation.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing N-aryl ketimine through acid catalyzed dehydration. Background technique [0002] N-aryl ketimine compounds are an important class of organic compounds, which can be used as ligands to form a variety of complexes, used in many aspects such as catalysis and dyes, and can also be used as intermediates for the synthesis of secondary amines by catalytic hydrogenation, such as Synthesis of chiral pesticide metolachlor (WO 9521151, WO 9705095). Generally, the synthesis of N-aryl ketimines requires long-time reactions (Dalton Trans. 2003, 3500; Chem EurJ 2004, 10, 267.) or metered dehydrating agents (New J. Chem. 2005, 29, 385. ), dehydration in the presence of tetra(ethoxy)titanium, titanium tetrachloride, etc., the post-treatment is cumbersome and the yield is low, which is not suitable for large-scale preparation. Contents of the invention ...

Claims

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Application Information

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IPC IPC(8): C07C249/00C07C251/24
Inventor 林双政宁斌科李勇智卫天琪张媛媛王列平王安勇张晓光王月梅
Owner XIAN MODERN CHEM RES INST
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