Synthetic method of 2-chloro-4-phenyl quinazoline

A technology of phenylquinazoline and synthesis method, which is applied in the synthesis field of 2-chloro-4-phenylquinazoline, can solve the problems of harsh reaction conditions, high cost, unsuitability for mass production, etc., and achieves simple aftertreatment. , the effect of cheap and easy to obtain reagents

Inactive Publication Date: 2017-08-22
CHANGZHOU UNIV
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Problems solved by technology

This synthetic method involves Suzuki coupling, the reaction conditions are relatively harsh, the cost is high, and it is not suitable for mass production

Method used

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  • Synthetic method of 2-chloro-4-phenyl quinazoline

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Embodiment Construction

[0015] (1) Synthesis of o-benzoylbenzoyl chloride 2

[0016] Add o-benzoylbenzoic acid (50 g, 221 mmol (mmol)) into a 500 mL round bottom flask, then add 150 mL of thionyl chloride to dissolve it, and heat to reflux for 1 hour (TLC tracking). After the reaction, the thionyl chloride was evaporated to dryness under reduced pressure at 60°C to obtain 259 g of a brownish-yellow oily substance, which was directly used in the next step without purification.

[0017] (2) Synthesis of o-benzoyl benzamide 3

[0018] Add 150mL of ammonia water into a 500mL three-necked flask, ice bath for 20 minutes, dissolve 2 (59g, 241mmol) in 100mL of acetonitrile, slowly drop into the three-necked flask, and react at room temperature for 1.5h (TLC tracking). After the reaction was completed, it was transferred to a round bottom flask, and the acetonitrile was evaporated to dryness under reduced pressure at 50° C., and a white solid appeared, and then 200 mL of water was added for washing, and suct...

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Abstract

The invention relates to a synthetic method of 2-chloro-4-phenyl quinazoline and belongs to the technical field of organic synthetic chemistry. The synthetic method comprises the following steps of: by taking o-benzoylbenzoic acid as a raw material, performing an acylating chlorination reaction to generate o-benzoyl benzoyl chloride; performing an amidation reaction to generate o-benzoyl benzamide; performing a Hofmann degradation reaction to generate 2-amino benzophenone; and performing an annulations reaction to generate 4-phenyl quinazoline-2(1H)-one and chlorinating the 4-phenyl quinazoline-2(1H)-one by phosphorus oxychloride to finally generate 2-chloro-4-phenyl quinazoline, wherein the total yield is 20.8%. Compared with other methods, the reagents used by the route are low in price and easily available, and the post-treatment is simple. In the reaction process, the reaction conditions and synthetic processes thereof are explored, so that a simple and feasible synthetic route is provided for synthesizing 2-chloro-4-phenyl quinazoline, thereby realizing amplified production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry and relates to a synthesis method of 2-chloro-4-phenylquinazoline. Background technique [0002] Phenothiazine is a class of aromatic heterocyclic compounds containing electron-rich nitrogen and sulfur atoms. Due to the high degree of electron enrichment of phenothiazine compounds, conjugated polymer materials containing phenothiazine units, especially binary phenothiazine, are particularly It is beneficial to the injection and transport of holes, so phenothiazine is considered to be a very good structural unit that can reduce the ionization potential of luminescent materials. Moreover, the most striking feature is that the phenothiazine molecule has a non-planar structure, which is quite different from the planar carbazole. Since the non-planarity of phenothiazine molecules can prevent the formation of intermolecular excimer compounds that reduce the quantum efficiency of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/78
CPCC07D239/78
Inventor 胡昆吴冬冬任杰
Owner CHANGZHOU UNIV
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