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New method for synthesizing ethylhydrazine dihydrochloride

A technology of dihydrochloride and synthesis method, which is applied in the field of synthesis of ethylhydrazine dihydrochloride, can solve the problems of unavailable raw materials and low yield, and achieve the goals of easy availability of raw materials, high yield and reduction of by-products generated effect

Active Publication Date: 2021-04-09
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] Moberg, William Karl et al reported the synthesis method of ethylhydrazine dihydrochloride in the patent EP2700634, the synthesis route is shown in the figure below, the disadvantage is that the raw materials are not easy to get , low yield

Method used

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  • New method for synthesizing ethylhydrazine dihydrochloride
  • New method for synthesizing ethylhydrazine dihydrochloride
  • New method for synthesizing ethylhydrazine dihydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 100ml of acetonitrile, 20.00g of acetylhydrazide, 22.14g of anhydrous sodium acetate and 1.32g of chloro[1,3-bis(2,6-diisopropylphenyl)imidazole-2 into a 250ml four-neck round bottom flask at 0°C - Subunit] copper (I), temperature controlled dropwise addition of 58.84g of bromoethane, raised to 20°C and stirred for 12h after dropping, suction filtered and evaporated to remove the solvent to obtain 23.00g of acetyl ethylhydrazine, yield 83.42%.

Embodiment 2

[0041] Add 100ml tetrahydrofuran, 20.00g acetylhydrazide, 36.74g potassium dihydrogen phosphate and 1.32g chloro[1,3-bis(2,6-diisopropylphenyl)imidazole-2 to a 250ml four-neck round bottom flask at 0°C - Subunit] copper (I), temperature controlled dropwise addition of 58.84g bromoethane, raised to 20°C and stirred for 12h after dripping, filtered with suction, evaporated the solvent under reduced pressure to obtain 24.37g acetyl ethyl hydrazine, the yield was 88.39 %.

Embodiment 3

[0043] Add 100ml of methanol to a 250ml four-neck round-bottom flask, add 20g of acetylethylhydrazine at 20°C, add 49.64g of concentrated hydrochloric acid dropwise, raise the temperature to 60°C and stir for 4h after the dropwise, evaporate the solvent under reduced pressure to obtain 25.97g of ethyl hydrazine Hydrazine dihydrochloride, yield 99%.

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Abstract

The invention provides a new synthesis method of ethylhydrazine dihydrochloride, and the method comprises the following steps: using acethydrazide which is simple and easy to prepare as a raw material, reacting acethydrazide with bromoethane in the presence of a catalyst to generate N-acetyl-N'-ethylhydrazine, and removing acetyl in hydrochloric acid under a strongly acidic condition to obtain the ethylhydrazine dihydrochloride product. The product structure is confirmed by 1H NMR and single crystal, the raw materials of the method are cheap and easily available, the production cost can be greatly reduced, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Specifically relate to the synthetic method of ethylhydrazine dihydrochloride. Background technique [0002] Ethylhydrazine dihydrochloride, CAS registration number is 49540-34-3, its chemical structure is as follows: [0003] [0004] Ethylhydrazine is a liquid with a boiling point of 107.9±9.0°C at normal pressure. It is highly toxic and is an important intermediate for the synthesis of 1-ethyl-5-hydroxypyrazole. 1-Ethyl-5-hydroxypyrazole is used as an intermediate for active compounds in agricultural chemicals, especially for the preparation of herbicides; it can also be used in the synthesis of pyridine-2-amino-1,2,4-thiadiazole derivatives as a glucokinase activator in the treatment of diabetes. Commercial products mainly exist in the form of hydrochloride, dihydrochloride and oxalate. [0005] Brown, Robert D. and Kearley, Robert A. reported in the literature Journal of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/14C07C241/02C07C241/04C07C243/28
CPCC07C241/02C07C241/04C07C243/14C07C243/28
Inventor 陈辉徐凤波李庆山祝冠彬王红学李娇王泽春
Owner NANKAI UNIV
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