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A kind of synthetic method of 2,4-dichloroquinazoline

A technology of dichloroquinazoline and synthesis method, applied in chemical instruments and methods, physical/chemical process catalysts, metal/metal oxide/metal hydroxide catalysts, etc., capable of solving environmental pollution, long reaction steps, and reaction products Low efficiency and other problems, to achieve the effect of safe operation, low cost and high yield

Active Publication Date: 2019-01-15
BINZHOU YUNENG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the aniline / phenoxycarbonyl isocyanate method and the anthranilic acid / potassium cyanate method are commonly used, both of which require the use of chlorinating agents such as restricted phosphorus oxychloride, which are highly corrosive. , these methods have the disadvantages of high toxicity of raw materials, difficulty in obtaining, long reaction steps, low reaction yield and serious environmental pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] A kind of synthetic method of 2,4-dichloroquinazoline, comprises the following steps:

[0019] 1) Mix anthranilyl chloride, carbon tetrachloride, pyridine, catalyst, methyl carbamate and DMSO, and the molar ratio of anthranilyl chloride, carbon tetrachloride and methyl carbamate is 1:1: 1, catalyst consumption is 3% of the quality of anthranilyl chloride, and the consumption of pyridine is 3 times of the molar number of anthranilyl chloride;

[0020] 2) React the mixture at 100°C and 0.2MPa for 5h;

[0021] 3) Then raise the temperature of the mixture to 200°C, and continue the reaction at 0.6MPa for 20-25h to end;

[0022] 4) After cooling, remove the insoluble matter by filtration, then pour the filtrate into water, add ethyl acetate for extraction, dry the organic phase with anhydrous calcium chloride and concentrate to obtain a white solid, namely 2,4-dichloroquinazoline, producing The rate is 97.0%.

[0023] The catalyst used in this example is made of the follo...

Embodiment 2

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

[0026] 1) Mix anthranilyl chloride, carbon tetrachloride, pyridine, catalyst, methyl carbamate and DMF, and the molar ratio of anthranilyl chloride, carbon tetrachloride and methyl carbamate is 1:1.05: 1.1, catalyst consumption is 5% of the quality of anthranilic acid chloride, and the consumption of pyridine is 3.12 times of the molar number of anthranilic acid chloride;

[0027] 2) React the mixture at 120°C and 0.3MPa for 7h;

[0028] 3) Then the mixture was heated to 230°C and 0.8 MPa, and the reaction was continued for 25 h to end;

[0029] 4) After cooling, remove the insoluble matter by filtration, then pour the filtrate into water, add chloroform for extraction, dry the organic phase with anhydrous sodium sulfate and concentrate to obtain a white solid, namely 2,4-dichloroquinazoline, with a yield of 99.1%.

[0030] The catalyst used in this example is made of the following...

Embodiment 3

[0032] A kind of synthetic method of 2,4-dichloroquinazoline, comprises the following steps:

[0033] 1) Mix anthranilyl chloride, carbon tetrachloride, 4-picoline, catalyst, methyl carbamate and tetrahydrofuran, and the molar ratio of anthranilyl chloride, carbon tetrachloride and methyl carbamate is 1:1.02:1.05, catalyst consumption is 4% of the quality of anthranilic acid chloride, acid-binding agent, and the consumption of 4-picoline is 3.1 times of the anthranilic acid chloride molar number;

[0034] 2) React the mixture at 110°C and 0.25 MPa for 6 h;

[0035] 3) Then the mixture was heated to 210°C, and the reaction was continued for 22 hours at 0.7MPa to end;

[0036] 4) After cooling, remove the insoluble matter by filtration, then pour the filtrate into water, add diethyl ether for extraction, dry the organic phase with anhydrous magnesium sulfate and concentrate to obtain a white solid, namely 2,4-dichloroquinazoline, with a yield of 98.5%.

[0037] The catalyst us...

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Abstract

The invention discloses a synthesis method of 2,4-dichloro quinazoline. The synthesis method comprises the following steps: (1) mixing o-amino benzoyl chloride, carbon tetrachloride, an acid-binding agent, a catalyst, methyl carbamate and an organic solvent; (2) enabling reaction at 100 to 120 DEG C and 0.2 to 0.3 MPa for 5 to 7 hours; (3) heating to 200 to 230 DEG C, and continuously enabling reaction at 0.6 to 0.8 MPa for 20 to 25 hours; (4) filtering out insolubles, and extracting filtrate to obtain white solids. Compared with the prior art, the synthesis method disclosed by the invention has the advantages that the raw materials are readily available, the price is low, and the pollution is low; the reaction steps are relatively short, and one-step reaction is realized; furthermore, no high-toxicity and high-corrosiveness reactants are used, so that the operation is safe; the yield is high and can reach 97.0 percent or above.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2,4-dichloroquinazoline. Background technique [0002] 2,4-Dichloroquinazoline is an important pharmaceutical and fine chemical intermediate, which has a wide range of biological and pharmaceutical activities and can be used for anticancer, bactericidal, insecticidal, anti-inflammatory, analgesic, sedative, antihypertensive, Antidiabetic and antiviral fields. With the increasing demand for downstream products of 2,4-dichloroquinazoline, its market prospect is very broad. In the prior art, the aniline / phenoxycarbonyl isocyanate method and the anthranilic acid / potassium cyanate method are commonly used, both of which require the use of chlorinating agents such as restricted phosphorus oxychloride, which are highly corrosive. , These methods have the disadvantages of high toxicity of raw materials, difficulty in obtaining, long reaction ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/95B01J23/30
CPCB01J23/002B01J23/30B01J2523/00C07D239/95B01J2523/43B01J2523/47B01J2523/55B01J2523/67B01J2523/69
Inventor 王永张立攀王法云刘红伟章建军赵梦瑶张文杰周莉关炳峰罗蓓蓓杜瑞张亚勋任钊
Owner BINZHOU YUNENG CHEM