Method for preparing 2,3-dihydroquinazoline-4(1H)-one and derivative thereof

A technology of dihydroquinazoline and derivatives, applied in organic chemistry, chemical recovery, etc., can solve the problems of difficult biodegradation, complicated preparation process, high preparation cost, etc., and achieve high utilization rate, good selectivity, and low loss Effect

Active Publication Date: 2015-07-01
平邑现代中药产业园有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the preparation of 2 in the prior art, the acidic ionic liquid catalyst that exists in 3-dihydroquinazolin-4 (1H)-ketone and derivatives thereof causes the use amount is very big because acidity is lower, preparation The cost is high, the preparation process is complicated, and it ...

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  • Method for preparing 2,3-dihydroquinazoline-4(1H)-one and derivative thereof
  • Method for preparing 2,3-dihydroquinazoline-4(1H)-one and derivative thereof
  • Method for preparing 2,3-dihydroquinazoline-4(1H)-one and derivative thereof

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Experimental program
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Effect test

Embodiment 1

[0024] Add 5mmol isatoic anhydride, 5mmol aniline, 5mmol benzaldehyde and 0.4mmol high acidity ionic liquid catalyst respectively to 15ml of water and ethanol mixed solution (V (water): V (ethanol) = 1:2) with stirring In a 50ml single-necked bottle, the reflux reaction time was 12min, followed by TLC (thin plate chromatography). After the reaction was completed, a large amount of solids were precipitated after cooling to room temperature. The solids were crushed, left standing, and suction filtered. 2,3-Diphenyl-2,3-dihydroquinazolin-4(1H)-one, yield 94%. The filtrate was directly added with isatoic anhydride, aniline and benzaldehyde for reuse.

[0025] 2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-one: m.p.208~209℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=6.27(d, J=2.4Hz, 1H, CH), 6.68(t, J=7.2Hz, 1H, ArH), 6.75(d, J=8.0Hz, 1H, ArH), 7.16(t, J=7.2Hz, 1H, ArH), 7.24~7.33(m, 8H, ArH), 7.35(d, J=7.2Hz, 2H, ArH), 7.64(d, J=2.4Hz, 1H, NH), 7.70 (d, J=8.0Hz, 1H, ArH)

Embodiment 2

[0027] Add 5mmol isatoic anhydride, 5mmol aniline, 5mmol p-methoxybenzaldehyde and 0.5mmol high acidity ionic liquid catalyst to 15ml water and ethanol mixed solution (V (water): V (ethanol) = 1:2) In a 50ml single-necked bottle with a stirrer, the reflux reaction time is 8min, TLC (thin plate chromatography) tracking detection, after the reaction is completed, a large amount of solids are precipitated when cooled to room temperature, the solids are crushed, left to stand, and suction filtered, and the resulting filter residue is vacuum After drying, pure 2-p-methoxyphenyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one was obtained in a yield of 90%. The filtrate was directly added with isatoic anhydride, aniline and p-methoxybenzaldehyde and reused.

[0028] 2-p-methoxyphenyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one: m.p.204~206℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=3.64(s, 3H, OCH 3), 6.21(d, J=2.4Hz, 1H, CH), 6.69(t, J=7.6Hz, 1H, ArH), 6.76(d, J=8.0Hz, 1H, ArH), 6.88(d, J= 8.4Hz, ...

Embodiment 3

[0030] 5mmol isatoic anhydride, 5mmol p-chloroaniline, 5mmol p-tolualdehyde and 0.6mmol high acidity ionic liquid catalyst were respectively added to 25ml water and ethanol mixed solution (V (water): V (ethanol) = 1:2 ) in a 100ml single-necked bottle with a stirrer, the reflux reaction time is 20min, TLC (thin plate chromatography) tracking detection, after the reaction is completed, a large amount of solids are precipitated when cooled to room temperature, the solids are crushed, left standing, and suction filtered, the obtained filter residue Pure 2-p-chlorophenyl-3-p-methylphenyl-2,3-dihydroquinazolin-4(1H)-one was obtained after vacuum drying with a yield of 91%. Repeat use after directly adding isatoic anhydride, p-chloroaniline and p-tolualdehyde in the filtrate.

[0031] 2-p-chlorophenyl-3-p-methylphenyl-2,3-dihydroquinazolin-4(1H)-one: m.p.258~260°C; 1 H NMR (400MHz, DMSO-d 6 ): δ=2.23(s, 3H, CH 3 ), 6.24(d, J=2.4Hz, 1H, CH), 6.77(dd, J=7.6Hz, 2H, ArH), 7.11(s, 4H,...

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Abstract

The invention discloses a method for preparing 2,3-dihydroquinazoline-4(1H)-one and a derivative thereof and belongs to the technical field of organic chemical synthesis. In the preparation, the mole ratio of isatoic anhydride to aromatic amine to aromatic aldehyde is 1 to 1 to 1; the molar weight of a high-acidity ionic liquid catalyst is 8% to 12% of that of the used isatoic anhydride; the reflux reaction time is 4min to 30min; the volume dose of a mixed solution of reaction solvents water and ethanol is 3-6 times that of the isatoic anhydride; the reaction pressure is one atmospheric pressure; after the reaction is ended, a product is cooled to room temperature and subjected to suction filtration; the obtained filter residues are dried in vacuum to obtain pure 2,3-dihydroquinazoline-4(1H)-one and the derivative thereof. In comparison with a preparation method adopting other catalysts, the method disclosed by the invention has the characteristics of being relatively small in catalyst toxicity, recyclable in use, relatively good in biodegradability, environmentally friendly and economical during the overall preparation process, simple and convenient to operate, convenient for large-scale industrial production and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for preparing 2,3-dihydroquinazolin-4(1H)-one and derivatives thereof. Background technique [0002] 2,3-Dihydroquinazolin-4(1H)-one and its derivatives are a class of nitrogen-containing heterocyclic compounds with good biological activity and pharmacological activity. It has excellent biological activity in blood pressure, anti-rheumatic, anti-hypertensive, diuretic and other aspects, and has broad application prospects in medicine. In addition, they also have important applications in agriculture and can be used as fungicides, herbicides, etc. Therefore, the preparation of 2,3-dihydroquinazolin-4(1H)-one and its derivatives has attracted widespread attention. The traditional method for preparing 2,3-dihydroquinazolin-4(1H)-one and its derivatives is to use the "one-pot" method of three components under various catalytic systems, but this method is more or ...

Claims

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Application Information

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IPC IPC(8): C07D239/91
CPCY02P20/584C07D239/91
Inventor 岳彩波高学频吴胜华储昭莲
Owner 平邑现代中药产业园有限公司
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