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Stable isotope labelled sulfamethazine and synthesis method thereof

A technology of sulfabromomethazine and stable isotopes, which is applied in the field of stable isotope-labeled sulfabromethazine and its synthesis, can solve the problems of long synthesis process route, expensive raw materials, difficult production process, etc., and achieve short process route , good economy and mild process conditions

Active Publication Date: 2019-07-19
FOOD INSPECTION CENT OF CIQ SHENZHEN +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, due to the high price of stable isotope-labeled raw materials, the high cost, the difficulty in realizing the production process, how to ensure that the stable isotope atoms will not fall off during the production process, and technical difficulties such as product purification, the synthesis of stable isotope-labeled sulfabromomethazine Methods are rarely reported
Chinese patent document CN107879985A discloses a preparation method of stable isotope deuterium-labeled sulfonamides. The method is to prepare different stable isotope deuterium-labeled sulfonamides from benzene-D6 through a five-step reaction. The synthetic process route is longer and the yield lower, limiting the application

Method used

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  • Stable isotope labelled sulfamethazine and synthesis method thereof
  • Stable isotope labelled sulfamethazine and synthesis method thereof
  • Stable isotope labelled sulfamethazine and synthesis method thereof

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Embodiment 1

[0038] The synthetic process of stable isotope-labeled sulfabromomethazine is as follows:

[0039] S1. Under ice-salt bath and nitrogen protection, add aniline-D to the reaction vessel 5 (17.96mmol, 1.76g), acetic anhydride (39.56mmol, 3.72mL) was added dropwise at 1 drop / second, reacted at 25-30°C for 2.5 hours, neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phase was saturated Washing with brine, and removing the solvent from the organic phase to obtain acetaminophen-D 5 , yield 99%;

[0040] S2. Under ice-salt bath and nitrogen protection, add acetaminophen-D to the reaction vessel 5 (17.16mmol, 2.41g), chlorosulfonic acid (184mmol, 12.3mL) was added dropwise at 2 drops / second, reacted at 25-30°C for 3 hours, placed again in an ice-salt bath, and added dropwise at 2 drops / second on ice Water (278mmol, 5mL), the precipitated solid was filtered, the filter cake was washed with water, and the filter cake was dried at ...

Embodiment 2

[0045] The synthetic process of stable isotope-labeled sulfabromomethazine is as follows:

[0046] S1. Under ice-salt bath and nitrogen protection, add aniline-D to the reaction vessel 5 (15mmol, 1.5g), acetic anhydride (30mmol, 2.8mL) was added dropwise at 2 drops / second, reacted at 25-30°C for 4 hours, neutralized with saturated sodium bicarbonate solution, extracted with dichloromethane, organic phase saturated saline After washing, the organic phase removes the solvent to obtain acetaminophen-D 5 , yield 98%;

[0047] S2. Under ice-salt bath and nitrogen protection, add acetaminophen-D to the reaction vessel 5 (12mmol, 1.7g), chlorosulfonic acid (120mmol, 8mL) was added dropwise at 1 drop / second, reacted at 25-30°C for 4 hours, placed under ice-salt bath again, and ice water was added dropwise at 2 drops / second ( 250mmol, 4.5mL), precipitated solid, filtered, washed the filter cake with water, and dried the filter cake at 70-80°C for 2-3 hours to obtain p-acetamidobenze...

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Abstract

The invention discloses stable isotope labelled sulfamethazine and a synthesis method thereof. The synthesis method comprises the following steps: S1: enabling stable isotope labelled aniline and acetic anhydride to react to prepare stable isotope labelled acetyl aminobenzene; S2: enabling the stable isotope labelled acetyl aminobenzene to react with chlorosulfonic acid to obtain stable isotope labelled p-acetamidobenzene sulfonyl chloride; S3: enabling the stable isotope labelled p-acetamidobenzene sulfonyl chloride to react with 2-amino-4,6-dimethyl-5-bromine pyrimidine, hydrolyzing the formed intermediate under the alkaline condition, and obtaining the stable isotope labelled sulfamethazine. Compared with the prior art, the condition of the synthesis process is mild, the process is simple, the process route is short, a product is easy to separate and purify, the yield is high, the chemical purity and the abundance of the stable isotope of the obtained product are both 99% or higherand meet the requirements of a standard reagent used for quantitatively detecting sulfabromomethazine; the use value is high, and the economic efficiency of the stable isotope labelled sulfamethazineis excellent.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a stable isotope-labeled sulfabromethazine and a synthesis method thereof. Background technique [0002] Sulfabromomethazine is a long-acting sulfonamide veterinary drug used for the treatment of coccidiosis and various bacterial infections in poultry, pigs and cattle. [0003] Sulfonamides are mainly used clinically to prevent and treat infectious diseases. In addition, they are stable in nature, do not require food as raw materials, have large output, many varieties, low prices, easy to use, and sufficient supply. They are widely used in veterinary clinics and animal husbandry It is widely used as a feed additive or animal disease treatment drug. However, sulfa drugs can cause allergic reactions in humans and may be carcinogenic. With the development of society, the unreasonable use of sulfonamides, the potential threat of ecological environment pollution and human...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/69C07B59/00
CPCC07D239/69C07B59/002C07B2200/05
Inventor 岳振峰赵凤娟罗耀郭会陈武炼
Owner FOOD INSPECTION CENT OF CIQ SHENZHEN
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