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5-chloro-6-(chloromethyl) uracil and preparation method thereof

A technology of chloromethyl and uracil, applied in the field of 5-chloro-6-uracil and its preparation, can solve the problems of incomplete chlorination, long synthesis route and high synthesis cost, and achieves complete chlorination reaction and high cost Low, method-reliable effect

Inactive Publication Date: 2017-05-10
SICHUAN TONGSHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The first object of the present invention is to provide a kind of preparation method of 5-chloro-6-(chloromethyl)uracil, to solve existing 5-chloro-6-(chloromethyl)uracil synthesis method long synthetic route, The problem of high synthetic cost, incomplete chlorination, and low product purity, the preparation method of 5-chloro-6-(chloromethyl)uracil, uses ethyl acetoacetate as the starting material, through two-step chlorination First introduce chlorine atoms into the compound structure, and then close the ring with urea to obtain the target product, which has the advantages of easy-to-obtain raw materials, simple operation, reliable method, low cost, and suitable for industrial production.

Method used

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  • 5-chloro-6-(chloromethyl) uracil and preparation method thereof

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Embodiment 1

[0044] The method for preparing 5-chloro-6-(chloromethyl)uracil provided in this embodiment specifically comprises the following steps:

[0045] (1) At 0°C, add 100g of ethyl 4-chloroacetoacetate and 500ml of dichloromethane to the three-necked flask in turn, stir at 0°C, then slowly add 86.17g of sulfuryl chloride dropwise, keeping the temperature at 0-5°C , reacted for 8 hours, the reaction was completed, concentrated, and distilled under reduced pressure to obtain 75 grams of ethyl 2,4-dichloroacetoacetate;

[0046](2), at room temperature, sequentially add 10 grams of urea, 33.17 grams of ethyl 2,4-dichloroacetoacetate and 200 grams of polyphosphoric acid in the three-necked bottle in step (2), start the mechanical stirring, and heat up to 100 ° C, React for 16 hours, after the reaction is complete, cool down to 50°C, add 200ml of water, drop to 20-30°C, filter, rinse the filter cake with ethyl acetate, and dry to obtain light brown solid 5-chloro-6-(chloromethyl ) Uracil...

Embodiment 2

[0048] The method for preparing 5-chloro-6-(chloromethyl)uracil provided in this embodiment specifically comprises the following steps:

[0049] (1), with the step (1) in the embodiment;

[0050] (2), at room temperature, sequentially add 10 grams of urea, 33.17 grams of ethyl 2,4-dichloroacetoacetate and 200 grams of polyphosphoric acid in the three-necked bottle in step (2), start the mechanical stirring, and heat up to 100 ° C, React for 14 hours, after the reaction is complete, cool down to 50°C, add 200ml of water, drop to 20-30°C, filter, rinse the filter cake with ethyl acetate, and dry to obtain light brown solid 5-chloro-6-(chloromethyl ) uracil 21 grams.

Embodiment 3

[0052] The method for preparing 5-chloro-6-(chloromethyl)uracil provided in this embodiment specifically comprises the following steps:

[0053] (1), with the step (1) in the embodiment;

[0054] (2), at room temperature, sequentially add 10 grams of urea, 33.17 grams of ethyl 2,4-dichloroacetoacetate and 200 grams of polyphosphoric acid in the three-necked bottle in step (2), start the mechanical stirring, and heat up to 90 ° C, React for 16 hours, after the reaction is complete, cool down to 50°C, add 200ml of water, drop to 20-30°C, filter, rinse the filter cake with ethyl acetate, and dry to obtain light brown solid 5-chloro-6-(chloromethyl ) 19.5 grams of uracil.

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Abstract

The invention provides 5-chloro-6-(chloromethyl) uracil and a preparation method thereof. The preparation method comprises the following steps that 1, ethyl acetoacetate is used a raw material, 4-chloracetyl ethyl acetate is prepared through chlorination reaction and performs chlorination reaction to obtain 2,4-dichloracetyl ethyl acetate; 2, the 2,4-dichloracetyl ethyl acetate in the step 1 and urea react in an acidic solvent under the heating condition to prepare the 5-chloro-6-(chloromethyl) uracil. The method has the advantages that the raw material is easy to obtain, the operation is simple, and the method is reliable, low in cost and suitable for industrial production. The prepared 5-chloro-6-(chloromethyl) uracil has the advantages of high purity and the like, the purity is 96% or above, and the highest purity can be up to 99.4%.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to 5-chloro-6-(chloromethyl)uracil and a preparation method thereof. Background technique [0002] Colorectal cancer is the third most common cancer worldwide and the third leading cause of cancer death in both men and women in the United States. At least 500,000 patients worldwide die from the disease every year, and the incidence and mortality of colorectal cancer in my country are also increasing year by year. According to the big data research report on the analysis of malignant tumor incidence and death in my country in 2016, there are 331,000 new cases of colorectal cancer in my country every year, and the incidence rate ranks fourth among all malignant tumors; 159,000 patients die of the disease every year The death rate is the fifth leading cause of cancer death. Colorectal cancer has become the third most common malignant tumor in the United States, and more t...

Claims

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Application Information

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IPC IPC(8): C07D239/553
CPCC07D239/553
Inventor 李庚黄青春杨龙焦波白顺强
Owner SICHUAN TONGSHENG BIOTECH
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