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Synthetic method of stable isotope labeled aminophenylsulfone

A technology of stable isotope and synthesis method, which is applied in the synthesis field of stable isotope-labeled dapsone, can solve the problems of long reaction steps, high cost of raw material aniline and high reaction temperature

Active Publication Date: 2015-03-25
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are few public documents about the stable isotope-labeled dapsone synthesis route, and there is no domestic literature report. Foreign C.E.Blackburn reported the following in 1972. 14 Synthesis from C-aniline 14 The synthetic method of C labeled dapsone, but 14 C is a radioactive isotope with a short half-life, and strong radioactivity has great harm to the human body, and related synthetic compounds have been disabled; Peter M.Gannett reported in 2003 a method for synthesizing dapsone with deuterated aniline as a raw material. This method starts from deuterated aniline Starting from acetylation, acylation, oxidation, and hydrolysis to obtain dapsone, the reaction steps are long, the raw material aniline is expensive, and precursors such as acetic anhydride are used in the reaction process, and the protection and deprotection process produces A large amount of waste acid and alkali cause great harm to the environment. The reaction process involves operations such as strong alkali and high temperature, and there is a small dilution of the abundance of the synthesized dapsone
WOKO patented an exchange method in 2008 to prepare deuterium-labeled dapsone. The exchange time is long, the reaction temperature is high, and the final abundance is only 47%.

Method used

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  • Synthetic method of stable isotope labeled aminophenylsulfone
  • Synthetic method of stable isotope labeled aminophenylsulfone
  • Synthetic method of stable isotope labeled aminophenylsulfone

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Experimental program
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Effect test

Embodiment 1

[0163] A stable isotope labeled dapsone-D 2 The preparation method comprises the following steps:

[0164] 1. Stable isotope labeling 4,4'-dinitrodiphenylsulfide-D 2 preparation of

[0165] Add 10.3g p-nitrobromobenzene-D to a 250mL three-necked flask 1 , add 20mL of water, stir and disperse, add 7g of sodium sulfide, add dropwise 50mL of 20% potassium carbonate aqueous solution at 0°C, after the dropwise addition is completed, rise to room temperature, react for 4 hours, filter with suction and wash with water to obtain 6.5g of light yellow 4,4 '-Dinitrodiphenylsulfide-D 2 , yield 93.5%, GC detection, purity 99.5%; mass spectrometry detection, abundance 99.5atom%D.

[0166] 2. Stable isotope labeling 4,4'-dinitrodiphenylsulfone-D 2 preparation of

[0167] In a 100mL three-necked flask, add 2.78g 4,4'-dinitrodiphenylsulfide-D 2 , add 5mL deuterated acetic acid, 3g potassium permanganate, control temperature at 0°C, react for 4 hours, pour into water, filter with suction...

Embodiment 2

[0172] A stable isotope labeled dapsone-D 1 The preparation method comprises the following steps:

[0173] 1. Stable isotope labeling 4,4'-dinitrodiphenylsulfide-D 1 preparation of

[0174] Add 5.1g p-nitrobromobenzene-D to a 250mL three-necked flask 1 , 4.5 p-nitrochlorobenzene, add 30mL of methanol and stir to dissolve, then add 1g of sodium methoxide under temperature control at -5°C, add 50mL of sodium sulfide aqueous solution dropwise, after the dropwise addition, control temperature at -5°C to 5°C, react for 2 hours, pour Pour into water, filter with suction and wash with water to obtain 6.3g light yellow 4,4'-dinitrodiphenylsulfide-D 1 , yield 91.5%, GC detection, purity 99.4%; mass spectrometry detection, abundance 99.2atom%D.

[0175] 2. Stable isotope labeling 4,4'-dinitrodiphenylsulfone-D 1 preparation of

[0176] In a 100mL three-necked flask, add 13.9g 4,4'-dinitrodiphenylsulfide-D 1 , add 50mL of deuterated chloroform, stir to dissolve, add 15mL of peracet...

Embodiment 3

[0181] A stable isotope labeled dapsone-D 4 The preparation method comprises the following steps:

[0182] 1. Stable isotope labeling 4,4'-dinitrodiphenylsulfide-D 4 preparation of

[0183] Add 14.5g p-nitrofluorobenzene-D to a 250mL three-necked flask 2 , add 30 mL of ethanol and stir to dissolve, then add 3 g of sodium ethoxide under temperature control at -5 ° C, add 50 mL of sodium sulfide aqueous solution dropwise, after the dropwise addition, control the temperature at 20 ° C for 5 hours, pour into water, filter with suction and wash with water to obtain 13.5 g of light yellow 4,4'-Dinitrodiphenylsulfide-D 4 , yield 96.4%, GC detection, purity 99.2%; mass spectrometry detection, abundance 99.3atom%D.

[0184] 2. Stable isotope labeling 4,4'-dinitrodiphenylsulfone-D 4 preparation of

[0185] In a 100mL three-necked flask, add 7g of 4,4'-dinitrodiphenylsulfide-D 4 , add 50mL deuterated acetonitrile, stir to dissolve, add 15g chromium trioxide, react at room temperat...

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Abstract

The invention relates to a synthetic method of stable isotope labeled aminophenylsulfone. The method comprises the following steps: by taking stable isotope labeled p-nitro halogeno benzene as a raw material, carrying out nucleophilic substitution to generate stable isotope labeled 4, 4'-dinitro phenyl sulfide; oxidizing to obtain stable isotope labeled 4, 4'-dinitro diphenyl sulfone; and finally carrying out reaction with a reducing agent to obtain the stable isotope labeled aminophenylsulfone. Compared with the prior art, according to the stable isotope labeled aminophenylsulfone prepared by the invention simply separated and purified, the chemical purity reaches over 99% and the isotope abundance is 99%, so that the demand of aminophenylsulfone detection of forbidden sulfonamides in the field of food safety can be fully satisfied.

Description

technical field [0001] The invention relates to a new synthesis method of stable isotope-labeled dapsone, in particular to a synthesis method of stable isotope-labeled dapsone. Background technique [0002] Dapsone (DDS), commonly known as: diaminodiphenylsulfone, diaminodiphenylsulfone, is a sulfone antibacterial agent, has a strong antibacterial effect on Bacillus leprae, and shows a bactericidal effect when used in large doses. Because its mechanism of action is similar to that of sulfa drugs, the two have a synergistic effect, and are often used as sulfa synergists in animals and aquaculture. However, dapsone is highly toxic and can cause blood system reactions, such as methemoglobinemia and hemolytic anemia, and may also cause liver and kidney damage and mental disorders. used, and shall not be detected in animal food; EU 2377 / 90 also clearly stipulates that dapsone is a prohibited drug. To prevent dapsone from entering the food chain, government surveillance agencies...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/36C07B59/00
Inventor 徐仲杰孙雯涂亚辉钟佳琪卢伟京杨超李美华
Owner SHANGHAI RES INST OF CHEM IND
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