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Preparation method of N-(2-propinyl)-glycolylurea

A hydantoin and propynyl technology, applied in the field of organic compound synthesis, can solve the problems of low reaction yield, high equipment requirements, poor economy and the like, and achieves high reaction yield, simple post-processing, and low equipment investment. Effect

Inactive Publication Date: 2012-03-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The raw materials of the first method are not easy to obtain, high toxicity, high cost and poor economy; in the second method, ethyl chloroformate and 3-chloropropyne are poisonous and flammable liquids, which are easy to cause explosion accidents, and are extremely unsafe to operate. Reaction yield is low (only 63%); Although the third method yield can reach 90.1%, used poisonous substance potassium cyanate reaction in the reaction process, bigger to environmental pollution; And because hydrobromic acid has strong corrosion non-toxic, easy to decompose, relatively high requirements for equipment

Method used

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  • Preparation method of N-(2-propinyl)-glycolylurea

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Effect test

Embodiment 1

[0028] Embodiment 1, a kind of preparation method of N-(2-propynyl)-hydantoin, take N-(2-propynyl)-N-ethoxycarbonylamino-acetonitrile as starting material, carry out successively The following steps:

[0029] (1) Add 16.6g (0.1mol) of N-(2-propynyl)-N-ethoxycarbonylamino-acetonitrile into a 250mL flask, add 33mL of water as a solvent, add 1mol of auxiliary liquid ammonia, and the mixture Divided into two phases, heated to 45-50°C, slowly added dropwise 16.7g of sodium hydroxide solution with a mass fraction of 30%, and the dropwise addition was completed in about 10 minutes, the reaction solution changed from two phases to homogeneous phase, and the color changed from orange to yellow Brown, gradually turning into dark brown, GC detects the reaction progress, continues to react for 5.5h, and the reaction temperature is 45~50℃;

[0030] (2) complete reaction, be cooled to 25 ℃ of room temperature, then use the hydrochloric acid solution neutralization reaction solution (to pH=...

Embodiment 2

[0031] Embodiment 2, a kind of preparation method of N-(2-propynyl)-hydantoin, take N-(2-propynyl)-N-ethoxycarbonylamino-acetonitrile as starting material, carry out successively The following steps:

[0032] (1) Add 16.6g (0.1mol) of N-(2-propynyl)-N-ethoxycarbonylamino-acetonitrile into a 250mL flask, 40mL of water as a solvent, and add an additive with a mass fraction of 30% hydrogen peroxide 22.6g, the mixed solution is divided into two phases, heated to 45-50°C, slowly added dropwise 16.7g of sodium hydroxide solution with a mass fraction of 30%, and the dropwise addition was completed in about 10 minutes, the reaction solution changed from two phases to a homogeneous phase, and the color From orange-yellow to brown, and gradually to dark brown, GC detects the reaction progress, and continues to react for 4.5 hours, and the reaction temperature is 45-50°C;

[0033] (2) After the reaction is completed, cool to room temperature at 25°C, then neutralize the reaction solutio...

Embodiment 3

[0034] Embodiment 3, a kind of preparation method of N-(2-propynyl)-hydantoin, take N-(2-propynyl)-N-ethoxycarbonylamino-acetonitrile as starting material, carry out successively The following steps:

[0035] (1) Add 16.6g (0.1mol) of N-(2-propynyl)-N-ethoxycarbonylamino-acetonitrile into a 250mL flask, add 50mL of water as a solvent, and drop in additives with a mass fraction of 30% over Hydrogen oxide 11.3g, the mixed solution is divided into two phases, heated to 45-50°C, slowly add 16.7g of sodium hydroxide solution with a mass fraction of 30%, and the dropwise addition is completed in about 10 minutes, and the reaction solution changes from two phases to a homogeneous phase , the color gradually changed from orange-yellow to dark yellow, GC detected the reaction progress, continued to react for 4.5h, and the reaction temperature was 45-50°C;

[0036] (2) complete reaction, be cooled to 25 ℃ of room temperature, then use the hydrochloric acid solution neutralization react...

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Abstract

The invention discloses a preparation method of N-(2-propinyl)-glycolylurea. The preparation method comprises the following steps of: (1) dissolving N-(2-propinyl)-N-carbethoxyl amino-acetonitrile into a solvent, adding an aid, heating to 20-80 DEG C, dropwise adding an alkaline catalyst, preserving heat and undergoing a ring-closure reaction; and (2) cooling the obtained reaction liquid to the room temperature, dropwise adding acid for neutralizing till the pH is 6-8, distilling under reduced pressure to remove ethanol serving as a byproduct, cooling to 0-10 DEG C, separating crystals out, preserving heat at 0-10 DEG C till no crystal can be separated out, and drying the crystals to obtain N-(2-propinyl)-glycolylurea. The N-(2-propinyl)-glycolylurea prepared with the method has the characteristics of simple process, safety for operating, high yield, low cost and low emission of three wastes.

Description

technical field [0001] The present invention relates to a kind of synthetic method of organic compound, especially N-(2-propynyl)-hydantoin (also known as hydantoin) (1-(prop-2-ynyl)imidazolidine-2,4- dione) synthesis method. Background technique [0002] N-(2-propynyl)-hydantoin, which has the formula C 6 h 6 o 2 N 2 , its structural formula is shown in S-1, the pure product is white to off-white crystal, melting point 124-125 ° C, slightly soluble in ethanol, ethyl acetate, almost insoluble in cold water, is an important fine chemical intermediate, in medicine , pesticides and chemical synthesis applications are particularly popular, mainly used for the synthesis of new high-efficiency hydantoin insecticides, disinfectants, and as optically active catalysts, peptizers and other products in chemical synthesis. [0003] [0004] [0005] According to comprehensive literature reports, the comparatively typical preparation method of hydantoin at present has: [000...

Claims

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Application Information

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IPC IPC(8): C07D233/74
Inventor 陈新志李桂花欧志安钱超王俊
Owner ZHEJIANG UNIV
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