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N,N'-bis(4-ethoxy carbonyl phenyl)-N'-benzyl formamidine

A technology of ethoxycarbonylphenyl and benzylformamidine is applied in the field of fine chemicals to achieve the effects of convenient operation, easy industrialized large-scale production, and easy separation and purification process

Active Publication Date: 2013-02-13
CHANGZHOU SUNLIGHT PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved in the present invention is: aiming at the problem of the production rate of the synthesis process of the existing N, N'-bis(4-ethoxycarbonylphenyl)-N'-benzylformamidine, to provide a high-yield N, N'-bis(4-ethoxycarbonylphenyl)-N'-benzylformamidine synthesis process

Method used

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  • N,N'-bis(4-ethoxy carbonyl phenyl)-N'-benzyl formamidine

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Dissolve 50g of ethyl 4-aminobenzoate in 104g of toluene under stirring, then raise the temperature to 43°C, add 18g of formic acid dropwise into the solution, and drop it for about 10 minutes, after stirring for two minutes, raise the temperature to 100°C to keep the system slightly After boiling for about 8 hours, the reaction was stopped, and the reaction solution was slowly cooled to room temperature, and a white solid was precipitated. Suction filtration, washing the solid three times with water, and drying to obtain 56 g of white intermediate ethyl 4-formamidobenzoate with a yield of 96%.

[0022] The resulting intermediate 4-formamidobenzoic acid ethyl ester was dissolved in 233gDMF to obtain a light yellow transparent solution, and 104g K was added thereto 2 CO 3 and 42g of benzyl chloride, then heated up to 60°C, reacted for 23h and cooled to room temperature, poured the reaction solution into water, precipitated a light yellow solid, filtered it with suction,...

Embodiment 2

[0025] Dissolve 99g of ethyl 4-aminobenzoate in 217g of toluene under stirring, then raise the temperature to 43°C, add dropwise 36g of formic acid into the solution, drop it for about 20 minutes, stir for two minutes, then raise the temperature to 100°C to keep the system slightly boiling After about 10 hours, the reaction was stopped, and the reaction solution was slowly cooled to room temperature, and a white solid was precipitated. Suction filtration, washing the solid three times with water, and drying to obtain 115 g of white intermediate ethyl 4-formamidobenzoate with a yield of 99%.

[0026] Gained intermediate 4-formamidobenzoic acid ethyl ester is dissolved in 378gDMF to obtain light yellow transparent solution, then adds 190g K thereto 2 CO 3 and 79g of benzyl chloride, then heated up to 60°C, reacted for 20h and then cooled to room temperature, poured the reaction solution into water, precipitated a light yellow solid, filtered it with suction, washed the solid wi...

Embodiment 3

[0029] Dissolve 99g of ethyl 4-aminobenzoate in 217g of toluene under stirring, then raise the temperature to 43°C, add dropwise 36g of formic acid into the solution, drop it for about 20 minutes, stir for two minutes, then raise the temperature to 100°C to keep the system slightly boiling After about 10 hours, the reaction was stopped, and the reaction solution was slowly cooled to room temperature, and a white solid was precipitated. Suction filtration, washing the solid three times with water, and drying to obtain 109 g of white intermediate ethyl 4-formamidobenzoate with a yield of 94%.

[0030] Gained intermediate 4-formamidobenzoic acid ethyl ester is dissolved in 378gDMF to obtain light yellow transparent solution, then adds 200g K thereto 2CO 3 and 81g of benzyl chloride, then heated up to 60°C, reacted for 23h and then cooled to room temperature, poured the reaction solution into water, precipitated a light yellow solid, filtered it with suction, washed the solid wit...

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Abstract

The invention relates to the technical field of fine chemistry industry, in particular to a method for preparing N, N'-di(4-ethoxycarbonylphenyl)-N'-phenylformamidine. Parathesin and benzyl chloride are taken as raw materials. The method comprises a formylation reaction process, an N alkylation reaction process and a condensation reaction process; wherein, in the N alkylation reaction process, 4-formamido ethyl benzoate generated in the formylation reaction process is added into dipolar aprotic solvent, and then inorganic weak base and the benzyl chloride are added, the temperature rises and is preserved and the reaction lasts for 20-25 hours; then the temperature is lowered to the room temperature and suction filtration and washing are carried out on the separated pale yellow solid to obtain pale yellow intermediate; the intermediate and the parathesin are added into halogenated hydrocarbon and then dehydrant is added; after heatingup and reflux for 15-17 hours, the temperature is cooled to the room temperature; NaOH aqueous solution is added to steam out the halogenated hydrocarbon under normal pressure and then separate out offwhite solid; suction filtration, washing by water and drying are carried out on the solid and the white solid of N, N'-di(4-ethoxycarbonylphenyl)-N'-phenylformamidine is obtained by recrystallization and cooling the solid to the room temperature after washing.

Description

Technical field [0001] The invention relates to the technical field of fine chemicals, in particular 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, dyes, textiles Adding this type of absorber to the synthetic process of ect., can avoid the destruction of the physical properties of the synthetic product caused by the photodegradation of ultraviolet rays (such as product discoloration, decolorization or brittle, easy to crack). In 1977, US4,021,471 reported that formamidine compounds could be used as ultraviolet absorbers and related synthesis techniques. The invention utilizes ethyl p-aminobenzoate to react with trialkyl orthoformate to prepare intermediate imide ester, and then reacts with N-alkylaniline to prepare formamidine....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C257/12C07C249/00
Inventor 胡国宜薛建伟闵雪峰缪文宏杨莉杨飞游劲松兰静波
Owner CHANGZHOU SUNLIGHT PHARMA
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