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Preparation method of N,N'-bis (4-ethoxycarbonylphenyl)-N'-benzyl formamidine

A technology of ethoxycarbonylphenyl and benzylformamidine is applied in the field of preparation of N,N'-bis(4-ethoxycarbonylphenyl)-N'-benzylformamidine, which can solve the problem of reaction Low yield, short synthetic route, reaction yield, long synthetic route, etc., to achieve the effect of shortening the synthetic route

Active Publication Date: 2015-07-22
CHANGZHOU YONGHE FINE CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to solve the technical problem of long synthetic route and low reaction yield in the prior art, and to provide a N,N'-bis(4-ethoxycarbonyl) with short synthetic route and high reaction yield The preparation method of phenyl)-N'-benzylformamidine

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0016] The preparation method of N,N'-bis(4-ethoxycarbonylphenyl)-N'-benzylformamidine in this example is as follows:

[0017] ①Condensation reaction: Add 150g of ethanol, 100g of ethyl p-aminobenzoate (0.61mol) and 50g of triethyl orthoformate (0.34mol) to the reaction device sequentially under stirring, slowly raise the temperature to 78°C, and maintain a slight reflux Status response 9h.

[0018] After the reaction, cool to room temperature, filter with suction, wash the filter cake with water, and dry to obtain 111 g of crude N,N'-bis(4-ethoxycarbonylphenyl)formamidine as an off-white solid.

[0019] The crude product was recrystallized with 166g of ethanol to obtain 90g of off-white solid N,N'-bis(4-ethoxycarbonylphenyl)formamidine with a purity of 99% (HPLC) and a yield of 86.5%.

[0020] ②N-Alkylation reaction: Add 200g of N,N-dimethylformamide (DMF) to another reaction device successively under stirring, and 90g of N,N'-bis(4 -Ethoxycarbonylphenyl)formamidine (0.262m...

Embodiment 2～ Embodiment 6）

[0025] Each embodiment is basically the same as Embodiment 1, and the differences are shown in Table 1.

[0026] Table 1

[0027] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 ethanol 150g 140g 160g 37g 76g 450g Ethyl p-aminobenzoate 100g 100g 100g 25g 50g 300g Triethyl orthoformate 50g 47g 52g 12g 26g 150g condensation reaction temperature 78℃ 77℃ 79℃ 78℃ 78℃ 78℃ Condensation reaction time 9h 10h 8h 9h 9h 9h Crude product of condensation reaction 111g 108g 105g 27g 50g 335g ethanol for recrystallization 166g 158g 165g 40g 75g 500g Condensation reaction product 90g 88g 87g 22g 44g 271g Condensation reaction product purity 99% 99% 99% 99% 99% 99% Condensation reaction yield 86.5% 84.6% 83.6% 84.6% 84.6% 86.8% DMF 200g 220g 174g 48g 97g 440g Condensation products for N-alkylation reactions 90g 88g 87g 22g 44g 271g ...

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Abstract

The invention discloses a preparation method of N,N'-bis (4-ethoxycarbonylphenyl)-N'-benzyl formamidine. The preparation method comprises the steps of carrying out condensation reaction on ethyl p-aminobenzoate and trialkyl ortho-formate to obtain N,N'-bis (4-ethoxycarbonylphenyl) formamidine; reacting benzyl chloride with the N,N'-bis (4-ethoxycarbonylphenyl) formamidine through N-alkylation reaction to obtain the N,N'-bis (4-ethoxycarbonylphenyl)-N'-benzyl formamidine, wherein the molar ratio of the ethyl p-aminobenzoate and the trialkyl ortho-formate is 1:0.3-1:0.7. According to the preparation method, two 4-ethoxycarbonylphenyls are grafted once, and only two reaction steps are required to obtain the N,N'-bis (4-ethoxycarbonylphenyl)-N'-benzyl formamidine, therefore, the synthetic route is greatly shortened, the total reaction yield can be up to more than 60%, and the preparation method is particularly suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to a preparation method of N,N'-bis(4-ethoxycarbonylphenyl)-N'-benzylformamidine. Background technique [0002] N,N'-bis(4-ethoxycarbonylphenyl)-N'-benzylformamidine is an important ultraviolet absorber, which is used in many organic materials such as plastic products, resin products, cosmetics, fuels, textiles The addition of the UV absorber in the synthetic process of UV rays can avoid the damage of the physical properties of the synthetic products (such as product discoloration, decolorization or fragility and cracking) caused by the photodegradation of ultraviolet rays. [0003] Chinese patent document CN1956947A discloses a kind of preparation method of N,N'-bis(4-ethoxycarbonylphenyl)-N'-benzyl formamidine. The method is based on ethyl p-aminobenzoate as raw material. Formylation reaction with formic acid, then N-alkylation reaction with benzyl bromide, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C257/12
Inventor 栾永勤陆海峰姜友林许晓春
Owner CHANGZHOU YONGHE FINE CHEM
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