Synthesis method of 2-chloro-4-phenylbenzoquinazoline

A benzoquinazoline and synthetic method technology, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, long reaction time, and low yield

Inactive Publication Date: 2020-07-07
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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Problems solved by technology

[0002] 2-Chloro-4-phenylbenzoquinazoline is a fine chemical raw material widely used in the synthesis of heterocyclic compounds. It is also an important OLED intermediate discovered in recent years. 2-Chloro-4-phenyl As an OLED intermediate, phenylbenzoquinazoline has great market potential in the world, but domestic production of such compounds is still relatively small.
[0003] At present, the synthesis method of 2-chloro-4-phenylbenzoquinazoline can be roughly divided into two categories: (1) use 2-benzoyl-1-naphthol as a raw material for amination, ring closure, and three steps of chlorination The final product is obtained by the reaction, and the amination reaction will use expensive 2-bromoisobutyramide. In fact, the amination reaction includes two-step reactions of electrophilic substitution and rearrangement, and the reaction time is relatively long. The biggest problem is 2-benzyl The raw material of acyl-1-naphthol is difficult to obtain. The synthetic route uses naphthol and benzoyl to do the Fuckers acylation reaction, which will have a great probability of going to the para position of the hydroxyl group, and it is difficult to obtain the ortho product. The required reaction The conditions are relatively harsh, and post-treatment produces a large amount of acid water, and the yield is not high; (2) obtained by coupling 2,4-dichlorobenzo[h]quinazoline with phenylboronic acid or phenylboronic acid pinacol ester 2-Chloro-4-phenylbenzoquinazoline, yield 50~60%, 2,4-dichlorobenzo[h]quinazoline raw material is more expensive and difficult to obtain in this method, and needs to use palladium Catalyst, the production cost will be relatively high

Method used

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  • Synthesis method of 2-chloro-4-phenylbenzoquinazoline
  • Synthesis method of 2-chloro-4-phenylbenzoquinazoline

Examples

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Effect test

Embodiment 1

[0025] A kind of synthetic method of 2-chloro-4 phenyl benzoquinazoline, comprises the following steps:

[0026] The first step: 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one

[0027] In a 500mL container, add 10.0g of 1-tetralone, 8.0g of benzaldehyde, 4.9g of urea, and 150ml of ethanol, add 8.9g of trimethylchlorosilane and 12.3g of sodium iodide under stirring, and heat up to 80°C for 2 hours. , cooled to room temperature and filtered after cooling down the reaction, and eluted the solid with a small amount of water and ethanol to obtain off-white solid 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one 11.8g , yield 62.42%;

[0028] The second step: Synthesis of 4-phenyl-1H-benzo[h]quinazolin-2-one:

[0029] In a 250mL container, add 11.8g of 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one synthesized in the first step above, 18.9g of DDQ, and 60ml of o-dichlorobenzene , raise the temperature to 70-75°C for 30 minutes, add 10.0g of DDQ, raise the temperature ...

Embodiment 2

[0033] A kind of synthetic method of 2-chloro-4 phenyl benzoquinazoline, comprises the following steps:

[0034] The first step: 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one

[0035] Add 10.0g of 1-tetralone, 8.0g of benzaldehyde, 4.9g of urea, 150ml of acetonitrile into a 500mL container, add 8.9g of trimethylchlorosilane and 12.3g of sodium iodide under stirring, and heat up to 80°C for 2 hours , cooled to room temperature and filtered after cooling down the reaction, and eluted the solid with a small amount of water and ethanol to obtain 9.5 g of off-white solid 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one , yield 50.26%;

[0036] The second step: Synthesis of 4-phenyl-1H-benzo[h]quinazolin-2-one:

[0037] In a 250mL container, add 11.8g of 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one synthesized in the first step above, 18.9g of DDQ, and 60ml of o-dichlorobenzene , raise the temperature to 70-75°C for 30 minutes, add 10.0g of DDQ, raise the temperat...

Embodiment 3

[0041] The first step: 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one

[0042]In a 500mL container, add 10.0g of 1-tetralone, 8.0g of benzaldehyde, 4.9g of urea, and 150ml of ethanol, add 10.4g of trimethylchlorosilane and 14.4g of sodium iodide under stirring, and heat up to 80°C for 2 hours , cooled to room temperature and filtered after cooling down the reaction, and eluted the solid with a small amount of water and ethanol to obtain 11.2 g of off-white solid 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one , yield 59.25%;

[0043] The second step: Synthesis of 4-phenyl-1H-benzo[h]quinazolin-2-one:

[0044] In a 250mL container, add 11.8g of 4-phenyl-3,4,5,6-tetrahydrobenzoquinazolin-2(1H)one synthesized in the first step above, 18.9g of DDQ, and 60ml of o-dichlorobenzene , raise the temperature to 70-75°C for 30 minutes, add 10.0g of DDQ, raise the temperature to 160-165°C for 2 hours, add 10ml of n-hexane to the system after the reaction is completely cooled dow...

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Abstract

The invention discloses a synthesis method of 2-chloro-4-phenylbenzoquinazoline, and belongs to the field of organic chemical synthesis. In the synthesis method, 1-tetralone, benzaldehyde and urea areused as raw materials, and thereby the 2-chloro-4-phenylbenzoquinazoline is obtained through three steps of reaction of bigeminy reaction ring closing, oxidation and chlorination. The method has theadvantages of low requirements on equipment and reaction conditions, accessible raw materials, low cost and short process period, and can greatly enhance the synthesis efficiency and economic benefit.

Description

technical field [0001] The invention relates to a synthesis method of 2-chloro-4-phenylbenzoquinazoline, which belongs to the field of chemical synthesis. Background technique: [0002] 2-Chloro-4-phenylbenzoquinazoline is a fine chemical raw material widely used in the synthesis of heterocyclic compounds. It is also an important OLED intermediate discovered in recent years. 2-Chloro-4-phenyl As an OLED intermediate, phenylbenzoquinazoline has great market potential in the world, but the domestic production of such compounds is still relatively small. [0003] At present, the synthesis method of 2-chloro-4-phenylbenzoquinazoline can be roughly divided into two categories: (1) use 2-benzoyl-1-naphthol as a raw material for amination, ring closure, and three steps of chlorination The final product is obtained by the reaction, and the amination reaction will use expensive 2-bromoisobutyramide. In fact, the amination reaction includes two-step reactions of electrophilic substit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/70
CPCC07D239/70
Inventor 柯标戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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