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Preparation method of di-tert-butyl iminodiacetate

A technology of iminodiacetic acid and tert-butyl chloroacetate is applied in the preparation of organic compounds, chemical instruments and methods, preparation of cyanide reaction, etc., and can solve the problems of complex reaction process, low catalyst and low yield, and achieves a high yield. The effect of high rate, low price and low industrial energy consumption

Inactive Publication Date: 2018-06-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The three main disadvantages of the above method are that the reaction process is complicated, the catalyst, and the yield are low.

Method used

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  • Preparation method of di-tert-butyl iminodiacetate
  • Preparation method of di-tert-butyl iminodiacetate
  • Preparation method of di-tert-butyl iminodiacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1, a kind of preparation method of di-tert-butyl iminodiacetate, carries out following steps successively:

[0041] In a 250mL three-necked flask equipped with a thermometer, a condenser and a stirrer, add 120mL of methanol, 120.0g of tert-butyl chloroacetate (0.8mol) and heat up to 65°C under mechanical stirring, and slowly introduce 5.1g of ammonia gas (0.3 mol), 2h pass through, insulation reaction 5h. Cool to room temperature after the reaction is completed, remove the white solid salt ammonium chloride produced by the reaction by filtration, and recover 110 mL of methanol by rotary evaporation of the filtrate. 41°C, yield 95.0%.

Embodiment 2

[0042] Embodiment 2, a kind of preparation method of di-tert-butyl iminodiacetate, carries out following steps successively:

[0043] In a 250mL three-necked flask equipped with a thermometer, a condenser and a stirrer, add 120mL of ethanol, 120.0g of tert-butyl chloroacetate (0.8mol) and heat up to 65°C under mechanical stirring, and slowly introduce 5.1g of ammonia gas (0.3 mol), 2h pass through, insulation reaction 5h. After the reaction, cool to room temperature, remove the white solid salt ammonium chloride produced by the reaction by filtration, and recover 112mL of ethanol by rotary evaporation of the filtrate. 41°C, yield 93.9%.

Embodiment 3

[0044] Embodiment 3, a kind of preparation method of di-tert-butyl iminodiacetate, carries out following steps successively:

[0045] In a 250mL three-necked flask equipped with a thermometer, a condenser and a stirrer, add 120mL of tert-butanol, 120.0g of tert-butyl chloroacetate (0.8mol) and heat up to 65°C under mechanical stirring, and slowly introduce 5.1g of ammonia gas (0.3mol), after 2h pass through, keep warm for 5h. After the reaction, cool to room temperature, remove the white solid salt ammonium chloride by filtration, and recover 108 mL of tert-butanol by rotary evaporation of the filtrate, cool the remaining liquid to 0°C, and filter the precipitated solid to obtain 22.6 g of di-tert-butyl iminodiacetate, melting point 41°C, yield 92.2%.

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Abstract

The invention discloses a preparation method of di-tert-butyl iminodiacetate. The method is characterized in that ammonia and tert-butyl chloroacetate are used as raw materials. The method comprises the following steps: carrying out a reaction between ammonia and tert-butyl chloroacetate based on the molar ratio of 1:(1-6) in an organic solvent under a closed condition, wherein the reaction temperature is 10-65 DEG C, the reaction pressure is normal pressure, and the reaction lasts for 2-10h; after the reaction ends, cooling until the room temperature is reached; filtering; rotatably evaporating the filtrate to remove the organic solvent; then cooling to reach the temperature of 0 DEG C to obtain a solid which is di-tert-butyl iminodiacetate. According to the method, the solvent is nontoxic and free of pollution; the solvent is recycled; no catalyst or cocatalyst is used; the reaction separation method is simple; the di-tert-butyl iminodiacetate yield is high.

Description

technical field [0001] The invention relates to a preparation method of a key pharmaceutical intermediate---di-tert-butyl iminodiacetate, which belongs to the field of organic synthesis. Background technique [0002] Camptothecin compound is now used as an anti-tumor drug, which has a significant curative effect on primary gastric cancer, liver cancer, rectal cancer, bladder cancer, leukemia, etc., and has extremely high medicinal value and huge market prospects. Di-tert-butyl iminodiacetate is an important intermediate for the synthesis of camptothecin compounds, and at the same time, it is also a key intermediate for the synthesis of chemical crosslinking agents and fluorine-containing chelating agents. Therefore, the synthesis of intermediate di-tert-butyl iminodiacetate has Great practical significance. [0003] So far, the synthetic method of di-tert-butyl iminodiacetate reported in the literature is mainly divided into the following types according to the difference o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/08C07C229/16
CPCY02P20/584C07C227/08C07C229/16
Inventor 陈新志牛石振钱超
Owner ZHEJIANG UNIV
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