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Method for synthesizing 1,4-diiodo-2-methoxy-5-nitrobenzene

A synthetic method, methoxy technology, applied in the preparation of amino compounds, chemical instruments and methods, and the preparation of amino compounds from amines, etc., can solve the problems of non-environmental protection, high cost, and many by-products, and achieve easy scale-up production and selection The effect of high stability and easy availability of raw materials

Inactive Publication Date: 2017-03-15
上海毕得医药科技股份有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

The technical problem solved by the present invention is: the existing 1,4-diiodo-2-methoxy-5-nitrobenzene preparation method has high cost, many by-products, and is not environmentally friendly

Method used

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  • Method for synthesizing 1,4-diiodo-2-methoxy-5-nitrobenzene

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Embodiment Construction

[0025] The technical solutions of the present invention are described below through specific examples, but the protection scope of the present invention is not limited thereto. The raw materials used and the actual are commercially available products.

[0026] (1) Preparation of Compound 2

[0027]

[0028] Add compound 1, 2-nitro-5-chloro-aniline (1500g, 8.7mol) to 15L of acetic acid, then add N-iodosuccinimide NIS (1957.0g, 8.7mol), and heat to 55°C After 2 hours of reaction, TLC detected that the reaction was complete. The reaction solution was cooled to 10°C, filtered, and the filter cake was washed with acetic acid, water and saturated sodium bicarbonate solution, and then washed with water until neutral. The crude product was dried to obtain Compound 2, namely 2-nitro-4-iodo-5-chloroaniline (2200 g, 7.4 mol), with a yield of 85%.

[0029] (2) Preparation of compound 3

[0030]

[0031] Compound 2, 2-nitro-4-iodo-5-chloroaniline (2200g, 7.4mol) was added to 7.3L...

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Abstract

The invention relates to the field of organic synthesis and discloses a method for synthesizing 1,4-diiodo-2-methoxy-5-nitrobenzene. The method includes the steps that firstly, 5-chloro-2-nitroaniline reacts with N-iodosuccinimide to generate 2-chloro-4-chloro-2-iodoaniline; secondly, alkali is added to 2-chloro-4-chloro-2-iodoaniline for reaction to obtain 3-methoxyl-4-iodo-5-nitroaniline; thirdly, 3-methoxyl-4-iodo-5-nitroaniline and p-toluene sulfonic acid are mixed, then a nitrite solution is dropwise added, a stirring reaction is conducted, then reaction liquid is dropwise added into a KI solution for reaction to generate 1,4-diiodo-2-methoxy-5-nitrobenzene. According to the synthesis method, raw materials are easy to obtain, reaction conditions are mild, selectivity is high, aftertreatment has good operability, the yield is high, production is easily enlarged, and the method is more environmentally friendly.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing and preparing a chemical intermediate 1,4-diiodo-2-methoxy-5-nitrobenzene compound. Background technique [0002] DNA sequencing technology is the basis for the study of genetic genome-related diseases. Sequencing by synthesis is a very important type of DNA next-generation sequencing technology. Sequencing-by-synthesis technology can effectively achieve massively parallel sequencing, greatly improving sequencing throughput and reducing costs, and has been widely used. In sequencing-by-synthesis, it is first necessary to synthesize fluorescein-labeled nucleotides as cyclic reversible terminals that can participate in DNA chain elongation. The reversible terminal structures reported in the literature mainly include two types: single-site modification (MRT) and double-site modification (DRT). The biggest advantage of the DRT type of reversible terminal ...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/36C07C209/68C07C209/74C07C211/52
CPCC07C201/12C07C209/68C07C209/74C07C205/36C07C211/52
Inventor 米淘冉黄良富陆琴杰张鋭豪李新玲
Owner 上海毕得医药科技股份有限公司
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