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Synthetic method of 4,6-dichloropyrimidine

A technology of dichloropyrimidine and a synthesis method, applied in directions such as organic chemistry, can solve the problems of high cost, cumbersome organic base recovery and reuse process, large amount of catalyst and the like, and achieves avoidance of waste, avoidance of product loss, and high product yield Effect

Inactive Publication Date: 2016-07-06
CHONGQING UNISPLENDOUR INT CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the above-mentioned shortcoming of the prior art, the object of the present invention is to provide a kind of synthetic method of 4,6-dichloropyrimidine, is used to solve the recovery and reuse process of organic base in the prior art loaded down with trivial details, the consumption of catalyst is big and high cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 (the content involved below is the mass content, DCP is the abbreviation of 4,6-dichloropyrimidine, and DHP is the abbreviation of 4,6-dihydroxypyrimidine)

[0028] In the device equipped with reflux condenser, thermometer, stirrer and constant pressure dropping funnel, add 4,6-dihydroxypyrimidine (114.3g, content 98%, 1mol), phosphorus oxychloride (1140g, 99%) Stir and mix evenly, raise the temperature to 95-100°C, and slowly add phosgene (220g, 99%, 2.2mol) to react, take a sample after 8h, and analyze by HPLC that the content of 4,6-dihydroxypyrimidine is 0.9%, 4,6- The content of dichloropyrimidine is 98.3%. After the reaction is completed, the reaction mixture is rectified under reduced pressure (oil bath temperature 95°C, vacuum degree-0.095MPa) to obtain 1082g of phosphorus oxychloride (content 99%); 4,6-dichloropyrimidine 142.8g (content 99.0%), yield 94.9% (calculated as 4,6-dihydroxypyrimidine), Wherein, W (DCP) refers to the quality of DCP, W (DHP...

Embodiment 2

[0030] In the device equipped with reflux condenser, thermometer, stirrer and constant pressure dropping funnel, add 4,6-dihydroxypyrimidine (114.3g, content 98%, 1mol), phosphorus oxychloride (600g, 99%) and nitrobenzene 1000mL, stir and mix evenly, heat up to 95-100°C, and slowly add phosgene (220g, 99%, 2.2mol) to react, take a sample after 7h, HPLC analysis 4,6-dihydroxypyrimidine content is 0.65 %, the content of 4,6-dichloropyrimidine was 97.8%, the reaction was completed, and the reaction mixture was rectified under reduced pressure (oil bath temperature 95°C, vacuum degree-0.095MPa) to obtain 565g of phosphorus oxychloride (content 99%); 4 , 6-dichloropyrimidine 140.0g (content 99.5%), yield 93.5% (based on 4,6-dihydroxypyrimidine).

Embodiment 3

[0032]Dissolve 212g of triphosgene (99%, 2.1mol) in 500mL of nitrobenzene for use; in a device equipped with a reflux condenser, a thermometer, a stirrer and a constant pressure dropping funnel, add 4,6-dihydroxypyrimidine (114.3g, content 98%, 1mol), phosphorus oxychloride (600g, 99%), stir and mix evenly, be warming up to 90-95 ℃, dropwise add the nitrobenzene solution of triphosgene, react sampling analysis after 6 hours, HPLC analysis 4,6-dihydroxypyrimidine content is 0.45%, 4,6-dichloropyrimidine content is 97.1%, after the reaction is completed, the reaction mixture is rectified under reduced pressure (oil bath temperature 95°C, vacuum degree-0.095MPa), to obtain Phosphorus oxychloride 565g (content 99%); 4,6-dichloropyrimidine 140.8g (content 99.7%), yield 94.2% (based on 4,6-dihydroxypyrimidine).

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Abstract

The invention provides a synthesis method of 4,6-dichloropyrimidine, comprising the following steps: 1) mixing 4,6-dihydroxypyrimidine with phosphorus oxychloride, and adding phosgene, diphosgene and triphosgene One or several combinations for reaction; 2) Separation and purification of the reaction solution obtained in step 1) to obtain phosphorus oxychloride and 4,6-dichloropyrimidine, and the recovered phosphorus oxychloride is used as a raw material for step 1) 4,6‑dichloropyrimidine synthesis reaction. The invention avoids the cumbersome process of organic alkali recovery and reuse, does not use expensive catalysts, avoids resource waste and product loss, is environmentally friendly, does not generate additional solid waste, and does not generate a large amount of phosphorus-containing waste liquid and waste residue, and the product yield is high, the purity is good, and it can meet the requirements of the market without secondary purification, and can be used for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a synthesis method of 4,6-dichloropyrimidine. Background technique [0002] Pyrimidine compounds have active molecular structures and are intermediates of many medicines and pesticides. Because of their important role in the field of pesticides and medicine, they have attracted the attention of many scholars. When used as a pharmaceutical intermediate, it is mainly used in the production of sulfa drugs, such as sulfamethazine, sulfamethiadiazole, sulfamotosine, sulfa-6-methoxine, etc. 4,6-dichloropyrimidine is also an important intermediate for the synthesis of sulfonamides and the fungicide azoxystrobin. [0003] There have been many reports in the literature on its preparation methods. The most common method is: react 4,6-dihydroxypyrimidine with tertiary amines such as triethylamine, pyridine, N,N-dimethylaniline, and phosphorus oxychloride at a certain temperature...

Claims

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Application Information

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IPC IPC(8): C07D239/30
CPCC07D239/30
Inventor 丁永良张飞刘佳何咏梅唐大家陈依柔刘文枚郑道敏
Owner CHONGQING UNISPLENDOUR INT CHEM
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