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Preparation system and preparation method of benzo quinazolinone derivative

A benzoquinazolone and preparation system technology, which is applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problem that the product yield needs to be further improved, it is not easy to industrialize large-scale production, and it can The number of recycling times is small, and the effect of high utilization of reaction raw materials, shortened reaction time, and economic cost savings is achieved.

Active Publication Date: 2017-10-24
东营睿港投资服务有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the large amount of catalyst loss, less recyclable times, difficult biodegradation, product purification and treatment before catalyst recycling when using acidic ionic liquids to catalyze and prepare benzoquinazolinone derivatives in the prior art. The process is complex and the reaction time is long, it is not easy to industrialize large-scale production, and the yield of the obtained product needs to be further improved. A preparation system and preparation method of benzoquinazolinone derivatives are provided

Method used

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  • Preparation system and preparation method of benzo quinazolinone derivative
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  • Preparation system and preparation method of benzo quinazolinone derivative

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preparation example Construction

[0035] A kind of preparation method of benzoquinazolinone derivative of the present invention, this method is to take aromatic aldehyde, ɑ-tetralone and urea or thiourea as reaction raw material, prepare under the catalysis of following catalyst:

[0036]

[0037] For the synthesis method of the catalyst used in the present invention, refer to related materials (Novel multi-SO3H functionalionic liquid for the conjugate addition of amines to electron deficientalkenes [J], Catalysis Communications, 2008, 10: 281-284).

[0038] The preparation method of benzoquinazolone derivative of the present invention, its chemical reaction formula is:

[0039]

[0040] Wherein, the molar ratio of the reaction raw materials aromatic aldehyde (I), ɑ-tetralone (II) and urea or thiourea (III) is 1:1: (1-1.4), and the molar amount of the catalyst is the aromatic 3~6% of aldehyde molar weight; Described reaction solvent adopts ethanol, and the volume of reaction solvent ethanol in milliliters ...

Embodiment 1

[0046] Add 1mmol benzaldehyde, 1mmolα-tetralone, 1mmol urea and 0.03mmol catalyst respectively into a 50ml single-necked bottle with a condenser tube containing 6ml ethanol, and stir evenly at room temperature. Heat to 80°C for 24 minutes under ultrasonic radiation, TLC (thin plate chromatography) detection, the raw material point disappears, after the reaction is completed, cool to room temperature to precipitate a large amount of solids, put it in an ice-water bath to continue cooling to precipitate solids, and grind when the amount of solids no longer increases Crush the precipitated solid, let it stand, filter with suction, wash the filter residue with ethanol (3ml×3), and dry it in vacuum to obtain 4-phenyl-3,4,5,6-tetrahydro-1H-benzo[h]quinazole The purity of the lin-2-one as determined by high performance liquid chromatography is 99.4%, and the calculated yield is 93%. Add benzaldehyde, ɑ-tetralone and urea directly to the filtrate of 6ml of washing liquid and then reus...

Embodiment 2

[0048] Add 1mmol benzaldehyde, 1mmolα-tetralone, 1mmol thiourea and 0.03mmol catalyst respectively into a 50ml single-necked bottle with a condenser tube containing 6ml ethanol, and stir evenly at room temperature. Heated to 80°C for 26 minutes under ultrasonic radiation, TLC (thin plate chromatography) detection, the raw material point disappeared, after the reaction was completed, cooled to room temperature to precipitate a large amount of solids, put it in an ice-water bath to continue cooling to precipitate solids, and grind when the amount of solids no longer increased Crush the precipitated solid, let it stand, filter with suction, wash the filter residue with ethanol (3ml×3), and dry it in vacuum to obtain 4-phenyl-3,4,5,6-tetrahydro-1H-benzo[h]quinazole Phenyl-2-thione, its purity determined by high performance liquid chromatography is 99.1%, and its calculated yield is 91%. Add benzaldehyde, ɑ-tetralone, and thiourea directly to the filtrate of 6ml of washing solution...

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Abstract

The invention discloses a preparation system and preparation method of a benzo quinazolinone derivative and belongs to the technical field of organic synthesis. The preparation system of the benzo quinazolinone derivative comprises a reactor, an ultrasonic-assisted reaction device, an ice-water bath cooling device, a suction filtration device, a washing device and a vacuum drying device, wherein the ultrasonic-assisted reaction device, the ice-water bath cooling device, the suction filtration device, the washing device and the vacuum drying device are sequentially arranged. Aromatic aldehyde, alpha-tetralone and urea or thiourea are taken as reaction raw materials and are catalyzed under the catalytic action of an acidic ionic liquid catalyst and under the ultrasonic-assisted action to prepare the benzo quinazolinone derivative. By adopting the technical scheme, the catalyst is relatively small in dosage and loss, and can be recycled for multiple times, the preparation system is high in raw material utilization rate and short in reaction time and a product is simple and convenient to purify.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation system and a preparation method of benzoquinazolinone derivatives. Background technique [0002] Benzoquinazolinone derivatives are a very important class of nitrogen-heterocyclic compounds. Due to their structural variability, they have a wide range of biological activities and are widely used in the fields of medicine and pesticides. In the field of medicine, they In addition to its main performance in antibacterial, antitumor, anticancer and antituberculosis, it also has the functions of sedation, anti-inflammation, hypnosis, anticonvulsion, regulating cardiovascular and regulating the activity of cells and enzymes. It is the research and development of new drugs and new pesticides. One of the hot spots. Therefore, it is of great significance to study the preparation of benzoquinazolone derivatives. [0003] Ionic liquids refer to...

Claims

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Application Information

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IPC IPC(8): C07D239/70B01J31/02
CPCB01J31/0285C07D239/70
Inventor 沈智培沈建忠
Owner 东营睿港投资服务有限责任公司
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