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Method for preparing methyl 4-(4'-aminophenylmethylene)phenylaminoformate

A technology of methyl phenylcarbamate and aminophenylmethylene, which is applied in the field of preparing monocarbamate to achieve the effects of easy control, easy availability of raw materials, and cost reduction

Inactive Publication Date: 2008-09-10
SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of this monocarbamate of 4-(4'-aminophenylmethylene) phenylcarbamate has not been reported yet.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 3.60g (0.04mol) of dimethyl carbonate and 3.96g (0.02mol) of diphenylmethanediamine in a 100mL autoclave equipped with magnetic stirring and ventilation tube, that is, dimethyl carbonate and diphenylmethane The substance ratio of diamine is 2:1, 0.18g of anhydrous zinc acetate (5mol% of diphenylmethanediamine), 30mL of benzene, the temperature is raised to 160°C, the air in the kettle is replaced by nitrogen gas, and the reaction is carried out under self-boosting pressure 1 hour. After cooling and suction filtration, the filter cake was recrystallized twice with methanol to obtain 0.45 g of a white crystalline solid.

[0026] Analysis methods such as infrared spectrum, mass spectrum, nuclear magnetic resonance and elemental analysis prove that the obtained white solid is methyl 4-(4'-aminophenylmethylene)phenylcarbamate.

[0027] The above reaction system was analyzed by high performance liquid chromatography, and the conversion rate of diphenylmethanediamine was ...

Embodiment 2

[0029] Add 3.60g (0.04mol) of dimethyl carbonate and 3.96g (0.02mol) of diphenylmethanediamine in a 100mL autoclave equipped with magnetic stirring and ventilation tube, that is, dimethyl carbonate and diphenylmethane The molar ratio of the diamine is 2:1, 0.28g of zinc octanoate (4mol% of diphenylmethanediamine), 35mL of toluene, the temperature is raised to 180°C, the air in the kettle is replaced by nitrogen gas, and the reaction is carried out for 0.5 hours under self-increasing pressure . After cooling and suction filtration, the filter cake was recrystallized twice with ethanol to obtain 0.37 g of a white crystalline solid.

[0030] Analysis methods such as infrared spectrum, mass spectrum, nuclear magnetic resonance and elemental analysis prove that the obtained white solid is methyl 4-(4'-aminophenylmethylene)phenylcarbamate.

[0031] The above reaction system was analyzed by high performance liquid chromatography, and the conversion rate of diphenylmethanediamine was...

Embodiment 3

[0033] Add 5.40 g (0.06 mol) of dimethyl carbonate and 3.96 g (0.02 mol) of diphenylmethanediamine in a 100 mL autoclave equipped with magnetic stirring and ventilation tube, that is, dimethyl carbonate and diphenylmethane The molar ratio of diamine is 3:1, zinc stearate 0.32g (2.5mol% of diphenylmethanediamine), ethylbenzene 30mL, the temperature is raised to 150°C, the air in the kettle is replaced by nitrogen gas, and the pressure is increased The reaction was carried out for 4 hours. After cooling and suction filtration, the filter cake was recrystallized three times with ethylene glycol to obtain 0.40 g of a white crystalline solid.

[0034] Analysis methods such as infrared spectrum, mass spectrum, nuclear magnetic resonance and elemental analysis prove that the obtained white solid is methyl 4-(4'-aminophenylmethylene)phenylcarbamate.

[0035] The above reaction system was analyzed by high performance liquid chromatography, and the conversion rate of diphenylmethanedia...

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PUM

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Abstract

The invention discloses a preparation method for 4-(4'-aminophenylmethylene) methyl N-phenylcarbamate. Methyl carbonate, diaminodiphenylmet hanes, solvent and catalyst are added into a reactor, the air in the reactor is replaced by aerating nitrogen, the self-pressure lifting is made at the reaction temperature between 150 and 180 DEG C, the reaction is made for 0.5 to 4 hours under the stirring, the mixture obtained after the reaction is filtered, then crystallization solvent is used to make two to three recrystallizations to the filter cake, white crystalloid solids precipitated at 30 DEG C are taken, and the solids are the target product. The method has the advantages of low cost, no pollution and simple preparation.

Description

technical field [0001] The invention belongs to a method for preparing monocarbamate, in particular to a method for preparing methyl 4-(4'-aminophenylmethylene)phenylcarbamate. technical background [0002] Carbamate compounds have a wide range of uses and can be used as pesticides, medicines, synthetic resin modification, intermediates in organic synthesis, and protection of amino groups in organic synthesis. In recent years, because it can generate isocyanate as an organic synthesis intermediate, carbamate compounds such as diphenylmethane dicarbamate, toluene-2,4-dicarbamate, etc. are of great industrial value. Synthesis has attracted much attention. At the same time, due to the relative stability of carbamate in various reaction systems and the reversibility of the formation reaction, it is being increasingly used for the protection of amino groups. [0003] The industrial production of carbamate still adopts the phosgene method which has many disadvantages. With the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/28C07C269/04
Inventor 王心葵邱泽刚王军威亢茂青李其峰
Owner SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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