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N-benzyl-benzoxazolone compound and synthesis method thereof

A technology of benzyl benzoxazolone and synthesis method, applied in the field of N-benzyl benzoxazolone compound and synthesis thereof, can solve the problems of high reaction conditions, unstable reactants, difficulty in operation and the like, and achieves The effect of high output, easy availability of raw materials and simple operation

Active Publication Date: 2017-09-22
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method does not react with electron-withdrawing groups, or requires higher reaction conditions
[0016] In summary, there are few methods for synthesizing N-benzylbenzoxazolone in the prior art, and some of them need to go through relatively complicated synthesis steps; question

Method used

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  • N-benzyl-benzoxazolone compound and synthesis method thereof
  • N-benzyl-benzoxazolone compound and synthesis method thereof
  • N-benzyl-benzoxazolone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] A kind of synthetic method of N-benzylbenzoxazolone compound, comprises the following steps:

[0057] A. Weigh 0.2mmol of benzoxazole, 0.6mmol of iodine, 0.6mmol of tert-butyl hydroperoxide (TBHP), 0.4mmol of toluene, and 2mL of chlorobenzene into a clean and dry reaction tube (with air inside), Seal the reaction tube, avoid contact with the outside atmosphere, stir and reflux at 110°C for 30 hours;

[0058] B. After stopping the reaction, cool to room temperature, extract 3 times with ethyl acetate and saturated brine, and dry the gained organic phase with anhydrous magnesium sulfate. 1) As a developing agent, it was separated and purified by column chromatography to obtain a white solid, namely 3-benzylbenzoxazol-2(3H)-one, with a yield of 87% and a melting point of 121-122°C.

[0059] Product structure:

[0060]

[0061] H NMR spectrum data of the product:

[0062] 1 HNMR (500MHz, CDCl 3 )δ7.36-7.30(m,5H),7.21-7.20(dd,J=5Hz,1H),7.10-7.07(m,2H),6.85-6.83(dd,J=...

Embodiment 2

[0066] A kind of synthetic method of N-benzylbenzoxazolone compound, comprises the following steps:

[0067] A. Weigh 0.2mmol of 5-methylbenzoxazole, 0.6mmol of iodine, 0.6mmol of tert-butyl hydroperoxide (TBHP), 0.4mmol of p-xylene and 2mL of chlorobenzene into a clean and dry reaction tube , (with air inside), seal the reaction tube, do not contact with the outside atmosphere, stir and reflux under the condition of 110 ℃ for 30 hours;

[0068] B. After stopping the reaction, cool to room temperature, extract 3 times with ethyl acetate and saturated brine, and dry the resulting organic phase with anhydrous magnesium sulfate, concentrate under reduced pressure, and dilute with petroleum ether:ethyl acetate (4:1) Used as a developer for column chromatography to separate and purify to obtain a white solid, 3-(4-methylbenzyl)-5-methylbenzoxazol-2(3H)-one, with a yield of 75% and a melting point of 108-109°C .

[0069] Product structure:

[0070]

[0071] H NMR spectrum data...

Embodiment 3

[0077] A kind of synthetic method of N-benzylbenzoxazolone compound, comprises the following steps:

[0078] A. Weigh 0.2mmol of benzoxazole, 0.6mmol iodine, 0.6mmol tert-butyl hydroperoxide (TBHP), 0.4mmol o-xylene and 2mL chlorobenzene into a clean and dry reaction tube, (there is Air), sealed reaction tube, not exposed to outside air, stirred and refluxed for 30 hours at 110°C;

[0079] B. After stopping the reaction, cool to room temperature, extract 3 times with ethyl acetate and saturated brine, and dry the gained organic phase with anhydrous magnesium sulfate. 1) As a developer, column chromatography was used for separation and purification to obtain a white solid, namely 3-(2-methylbenzyl)-benzoxazol-2(3H)-one, with a yield of 76% and a melting point of 130-131°C.

[0080] The product structure formula is:

[0081]

[0082] H NMR spectrum data of the product:

[0083] 1 HNMR (500MHz, CDCl 3 )

[0084] δ7.24-7.21(m,3H),7.20-7.15((m,2H),7.10-7.03(m,2H),6.72(d,J=...

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PUM

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Abstract

The invention provides an N-benzyl-benzoxazolone compound and a synthesis method thereof. Under the condition of sealed air, catalyzed without metal, a benzoxazolone compound directly reacts with a methylbenzene compound to prepare the N-benzyl-benzoxazolone compound. Compared with the prior art, the synthesis method is very simple and convenient, raw materials are easy to obtain, the cost is low, the efficiency is high, the method is suitable for various reaction substrates. Prepared products can be used for clinical drugs and drug intermediates capable of effectively treating diseases.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an N-benzylbenzoxazolone compound and a synthesis method thereof. Background technique [0002] Research has found that N-benzylbenzoxazolone compounds have high use value in the field of medicine and biopharmaceuticals. Benzoxazolones serve as a valuable pharmacophore in clinical drugs, drug candidates, and many of their compounds also have a wide range of biological activities. Studies have shown that N-benzylbenzoxazolone and its derivatives are a very common intermediate in the synthesis of analgesics, insecticides, herbicides, and antiepileptic drugs, and many of its derivatives have been used in life Or clinical medicine is widely used. For example, the following formula 1 is that phosalon is a pesticide; formula 2 is that besonprodil is an anti-Parkinson drug undergoing clinical trials; formula 3 is that SN79 is a drug candidate, mainly used for dru...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/58
CPCC07D263/58
Inventor 张武李倩史田超
Owner ANHUI NORMAL UNIV