Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing 2-bromo-4-nitroimidazole

A technology of nitroimidazole and bromine, applied in the field of synthesis of 2-bromo-4-nitroimidazole, can solve problems such as high price, long treatment time, residual heavy metal elements, etc., and is beneficial to industrialized production and reaction chemical selection. Good performance and mild reaction conditions

Active Publication Date: 2016-03-30
ZHEJIANG ZHUJI UNITED CHEM
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the treatment time of MDR-TB patients is at least 20 months, it brings great difficulties to patients' compliance with the treatment plan
From a global perspective, the treatment success rate of MDR-TB patients is less than 50% with only existing anti-tuberculosis drugs, which constitutes a very urgent medical need
The transition heavy metal Pt or Pd used in the catalytic hydrogenation deiodination reaction is not only expensive, but also concerns about their residual traces of heavy metal elements in the final product.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing 2-bromo-4-nitroimidazole
  • Method for synthesizing 2-bromo-4-nitroimidazole
  • Method for synthesizing 2-bromo-4-nitroimidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation of 2,5-dibromo-4-nitroimidazole

[0032] In a 20L reaction kettle equipped with mechanical stirring, reflux condenser and tail gas receiving device, add 4-nitroimidazole (1500g), distilled water (13L), sodium bicarbonate (2458g) respectively, stir, and control the temperature at 25 Bromine (1565 mL) was added dropwise within ℃. After the dropwise addition, raise the temperature to 50-55°C and continue stirring until the reaction is complete, stop heating, cool down to 5°C, and filter. The obtained solid was washed twice with distilled water and dried in vacuum to obtain 3198 g of yellow solid 2,5-dibromo-4-nitroimidazole.

Embodiment 2

[0033] Embodiment 2: Preparation of 2-bromo-5-iodo-4-nitroimidazole

[0034] In a 10-liter reactor equipped with mechanical stirring and reflux condensing device, add respectively 2,5-dibromo-4-nitroimidazole (1112g), sodium iodide (615g) and 6L distilled water and DMF mixed solution ( 4:1). Heat to reflux until the reaction is complete, cool to 5°C, filter, wash with distilled water twice, and dry in vacuum to obtain 1193 g of yellow solid 2-bromo-5-iodo-4-nitroimidazole.

Embodiment 3

[0035] Embodiment 3: Preparation of 2-bromo-4-nitroimidazole 11

[0036] In a 10-liter reactor equipped with mechanical stirring and reflux condenser, 2-bromo-5-iodo-4-nitroimidazole (1907 g) and absolute ethanol (3 L) were added respectively. Stir, slowly add diethyl phosphite (773mL), heat to reflux for 6 hours, evaporate most of the ethanol, cool to room temperature, add 1800mL concentrated ammonia water and 800g crushed ice, stir, then slowly add concentrated hydrochloric acid to adjust the pH to weak acidity, Cool to 5°C, filter, wash the filtered solid with distilled water, and vacuum-dry to obtain 1084 g of light yellow solid 2-bromo-4-nitroimidazole. 1HNMRδppm (400MHz, DMSO-d 6 ): 14.14(br,1H), 8.44(s,1H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing 2-bromo-4-nitroimidazole. According to the method, 4-nitroimidazole (VIII) is taken as a raw material and reacts with a bromide reagent in water under the action of alkali metal bicarbonate, 2,5-dibromo nitroimidazole (XI) is obtained and reacts with an iodo-reagent in an aprotic solvent, and 2-bromo-5-iodo-nitroimidazole (XV) is obtained; 2-bromo-5-iodo-nitroimidazole (XV) further reacts with a phosphorus reduction reagent in an alcohol solvent, and a target product, namely, 2-bromo-4-nitroimidazole (II) is obtained. The method has the main benefits as follows: the overall technology is simple, reaction conditions are mild, the technology is safe, the yield is high, the product quality is high, and industrial production is facilitated.

Description

technical field [0001] The invention relates to a synthesis method of organic heterocyclic compounds, in particular to a synthesis method of 2-bromo-4-nitroimidazole. Background technique [0002] According to data reported by the World Health Organization, tuberculosis is the second leading cause of death among infectious diseases. Every year, the number of tuberculosis cases in the world is about 8.6 million, and nearly 1.3 million people die from tuberculosis or tuberculosis-related diseases (WHOGlobalTBreport2013, World Health Organization global tuberculosis report). The current treatment plan requires patients to take multiple drugs for a long time. Due to improper use of anti-tuberculosis drugs, including untimely supply of drugs, poor quality of drugs, or failure of patients to complete the course of treatment according to the treatment plan, many patients develop therapeutic drug resistance or even multi-drug resistance. Tuberculosis (MDR-TB). The emergence of mul...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D233/92
CPCC07D233/92
Inventor 周萍周君津陈邦池
Owner ZHEJIANG ZHUJI UNITED CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com