Synthesis method of nitrile compound

A synthesis method and compound technology, applied in the field of biomedicine, can solve the problems of medium yield, unsuitable for large-scale industrial production, etc., and achieve the effects of good functional group tolerance and short reaction time

Pending Publication Date: 2022-04-29
CHONGQING MEDICAL UNIVERSITY
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  • Abstract
  • Description
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Problems solved by technology

Varvounis et al. (Synlett 2007, (17), 2671-2674.) reported the thermal dehydration of aldoximes to nitriles with the assistance of N,N-dimethylformamide, however the reaction took 48 hours with moderate yields
In addition, Sharwan et al. (Arkivoc 2006,41-44.) reported a o

Method used

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  • Synthesis method of nitrile compound
  • Synthesis method of nitrile compound
  • Synthesis method of nitrile compound

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Experimental program
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Effect test

Embodiment 1

[0045] The general preparation steps that the present invention obtains are:

[0046] Add formula I compound, formula II compound and imidazole hydrochloride in 10ml round bottom flask, place 120 ℃ of oil baths and heat reaction, monitor reaction progress by TLC, after reaction finishes, add 25ml saturated common salt water and make reaction cooling, and The resulting mixture was extracted four times with 20 ml of ethyl acetate, and the combined organic layers were successively washed with anhydrous Na 2 SO 4 After drying, filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent: petroleum ether and ethyl acetate in a volume ratio of 6:1), and recrystallized from ethyl acetate and n-hexane to obtain the target product.

[0047]The inventor explored the reaction of 4-nitro-benzaldehyde (1a) and hydroxylamine hydrochloride (2a) to synthesize 4-nitrobenzonitrile (3a), and the results are listed in Table 1. The ini...

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PUM

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Abstract

The invention provides a synthetic method of a nitrile compound, which is characterized in that imidazole hydrochloride is used as a reaction aid, and the nitrile compound is synthesized from an aldehyde compound and hydroxylamine hydrochloride by a one-pot method in the absence of other catalysts or additives. The synthesis method disclosed by the invention has good functional group tolerance and can be used for synthesizing various nitrile compounds. According to the synthesis method, corrosive concentrated hydrochloric acid and a metal catalyst are not used, strict reaction conditions, gas protection and an autoclave are not needed, the reaction time is short, and the synthesis method has important value in industrial production.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a method for synthesizing nitrile compounds. Background technique [0002] Nitrile compounds are organic compounds connected by carbon atoms containing hydrocarbon groups and cyano groups. They are a type of organic matter containing organic groups-CN and are also important chemical raw materials. They are widely used in synthetic resins, fibers, rubber, medicines, and pesticides. It is also used in industries such as electroplating, steel quenching and mineral processing. At present, nitrile compounds can be prepared by haloalkane cyanation, ammoxidation, carboxyl nitrile, acetonitrile addition, acrylonitrile, etc. Most of these methods use highly toxic cyanation reagents (such as sodium cyanide, potassium cyanide, etc.) , high temperature and high pressure conditions, toxic reagents, strong oxidants or metal catalysts. From the perspective of green chemistry, there is an ...

Claims

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Application Information

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IPC IPC(8): C07C255/50C07C253/00C07D319/18C07D207/34C07D333/38C07D213/84C07D209/42C07C255/52C07C255/33C07C255/03C07C255/53C07C255/54C07C255/58C07C255/57C07C319/20C07C323/62
CPCC07C253/00C07D319/18C07D207/34C07D333/38C07D213/84C07D209/42C07C319/20C07C2603/24C07C255/50C07C255/52C07C255/33C07C255/03C07C255/53C07C255/54C07C255/58C07C255/57C07C323/62
Inventor 袁建勇黄欣王印
Owner CHONGQING MEDICAL UNIVERSITY
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