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A method for preparing 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine

A technology of dimethylphenoxy and ethoxyethyl is applied in the field of synthesis of primary amine compounds and the preparation of 2-[4--2,3-dimethylphenoxy]ethylamine, which can Solve problems such as hidden safety hazards and difficult removal of secondary amines, and achieve the effects of cheap raw materials, easy availability of raw materials and simple reaction conditions

Active Publication Date: 2020-10-09
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process operation has strict requirements, and there are certain safety hazards, and the by-product of secondary amine is not easy to remove

Method used

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  • A method for preparing 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine
  • A method for preparing 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine
  • A method for preparing 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Preparation of 2-[4-(2-ethoxyethyl)phenoxy]ethylamine

[0020] step 1:

[0021] Add 29.3g (220mmol) of aluminum trichloride and 100g of dichloromethane to a 500mL four-necked flask, stir in an ice-water bath and cool down to 0-5°C for use. A solution of 9.4 g (100 mmol) of phenol (raw material 1) dissolved in 20 g of dichloromethane was added dropwise from the dropping funnel, and the temperature was controlled <10°C. Subsequently, a solution of 25.0 g (221 mmol) of chloroacetyl chloride dissolved in 20 g of dichloromethane was added dropwise from the dropping funnel, and the temperature was controlled <10°C. After dropping, remove the ice-water bath and stir at room temperature for 10 h.

[0022] The reaction solution was slowly transferred to a measuring cup equipped with 10% hydrochloric acid 500g, and a large amount of solids were precipitated. After fully stirring for 1h, it was filtered and rinsed with 200g of water. After the filter cake was dried, 2...

Embodiment 2

[0037] Example 2 Preparation of 2-[4-(2-ethoxyethyl)phenoxy]ethylamine

[0038] step 1:

[0039] With reference to the operation of the first step of Example 1, the reaction conditions were changed to obtain the results in Table 1.

[0040] Table 1

[0041]

[0042]

[0043] Step 2:

[0044]With reference to the operation of the second step of Example 1, the reaction conditions were changed to obtain the results in Table 2.

[0045] Table 2

[0046] experiment number Accelerator solvent temperature reflex yield 1 Sodium ethylate, 2.5eq ethanol 0°C to 25°C 90％ 2 Sodium ethylate, 2.5eq toluene 0°C to 25°C 63％ 3 Sodium ethylate, 2.5eq Tetrahydrofuran 0°C to 25°C 85％

[0047] Step 3:

[0048] With reference to the operation of the third step of Example 1, the reaction conditions were changed to obtain the results in Table 3.

[0049] table 3

[0050] experiment number Accelerator solvent temperature ...

Embodiment 3

[0064] Example 3 Preparation of 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine

[0065] step 1:

[0066] Add 29.3g (220mmol) of aluminum trichloride and 100g of dichloromethane to a 500mL four-necked flask, stir in an ice-water bath and cool down to 0-5°C for use. A solution of 12.2 g (100 mmol) of 2,3-dimethylphenol (raw material 1) dissolved in 20 g of dichloromethane was added dropwise from the dropping funnel, and the temperature was controlled <10°C. Subsequently, a solution of 25.0 g (221 mmol) of chloroacetyl chloride dissolved in 20 g of dichloromethane was added dropwise from the dropping funnel, and the temperature was controlled <10°C. After dropping, remove the ice-water bath and stir at room temperature for 7h.

[0067] The reaction solution was slowly transferred to a measuring cup equipped with 10% hydrochloric acid 500g, and a large amount of solids were precipitated. After fully stirring for 1h, it was filtered and rinsed with 200g of water. After the ...

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Abstract

The invention discloses a method for preparing 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine and belongs to the technical field of organic chemistry. The method takes 2,3-dimethylphenol as a rawmaterial and the raw material is sequentially subjected to the following steps: first-step reaction: chloroacetylation; second-step reaction: etherification; third-step reaction: reduction; fourth-step reaction: etherification; fifth-step reaction: ammoniation; sixth-step reaction: deprotection, so as to obtain the 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine. The method disclosed by the invention has the advantages that the raw material is cheap and easy to obtain, reaction conditions of each step are simple, the reaction selectivity is high and synthesis ways of pesticide intermediates are enriched.

Description

technical field [0001] The present invention relates to the synthesis of primary amine compounds, in particular to a method for preparing 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine, which belongs to organic chemical field. Background technique [0002] 2-[4-(2-ethoxyethyl)substituted phenoxy]ethylamine is an important intermediate for the synthesis of phenoxyethylaminopyrimidines and quinazolines. The compounds have good bactericidal, insecticidal and acaricidal effects, and are widely used in the field of agrochemicals. (See: US4304778, 1979; US4435402, 1982; EP0196524, 1986). [0003] The currently reported synthetic methods are as follows: [0004] Bromination of phenol derivatives to obtain para-bromine substituted phenol derivatives; further protection with chloroacetaldehyde dimethyl acetal to obtain phenol bromination derivatives protected by phenolic hydroxyl groups; further reaction with magnesium to prepare Grignard reagents; Ethane reacts to obtain th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/14C07C69/63C07C45/64C07C45/65C07C49/84C07C41/18C07C43/178C07C41/16C07C43/225C07C213/02C07C217/20C07D239/42C07D209/48A01P1/00A01P3/00A01P7/02A01P7/04
CPCC07C41/16C07C41/18C07C45/64C07C45/65C07C67/14C07C213/02C07D209/48C07D239/42C07C69/63C07C49/84C07C43/1783C07C43/225C07C217/20
Inventor 戴耀赵丹阳王荣良王延波
Owner DALIAN JOIN KING FINE CHEM CO LTD
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