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

Preparation of 1, 2, 4-triazole

A technology of reaction and phenyl, applied in the field of preparation of 1,2,4-triazole, can solve the problems of unfavorable experimental operation, industrial production, harsh reaction conditions, etc.

Active Publication Date: 2022-07-29
LANZHOU UNIVERSITY
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantages of this method include: (1) most of the reaction raw materials chloromethylene amide and hydrazide are not commercially available; (2) the reaction conditions are relatively harsh, such as the preparation of chloromethylene amide often using phosphorus oxychloride (POCl 3 ), which is not conducive to experimental operation and industrial production

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
  • Preparation of 1, 2, 4-triazole
  • Preparation of 1, 2, 4-triazole
  • Preparation of 1, 2, 4-triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: the preparation method of 3-amino-1,2,4-triazole:

[0021] Under argon, benzenesulfonyl hydrazone (0.2 mmol) was dissolved in 1,2-dichloroethane (3 mL), and NH was added. 2 CN (0.4 mmol), BF 3 ·OEt 2 (0.3 mmol), react at room temperature until the benzenesulfonyl hydrazone completely disappears (5-24 hours), the product is extracted with ethyl acetate (200 mL), and the organic phase is washed with saturated Na 2 CO 3 Solution wash, saline wash, anhydrous MgSO 4 After drying, the solvent was evaporated under reduced pressure, and 3-amino-1,2,4-triazole was obtained by column chromatography.

[0022] The spectral data are as follows:

[0023]

[0024] 14.9mg, 93% yield. 1 H NMR (400MHz, DMSO-d 6 )δ=12.05(brs,1H),7.91-7.88(m,2H),7.42-7.34(m,3H),6.07(brs,2H); 13 C NMR (100MHz, DMSO-d 6 )δ=158.4, 157.3, 132.3, 128.4, 128.1, 125.3ppm.

[0025]

[0026] 30.3mg, 87% yield. 1 H NMR (400MHz, DMSO-d 6 )δ=11.98(brs,1H),7.78(d,J=8.4Hz,2H),7.20(d,J=7.2...

Embodiment 2

[0055] Embodiment 2: The preparation method of 2-toluenesulfonyl-1,2,4-triazol-3-one:

[0056] Under argon protection, dissolve benzenesulfonylhydrazone (0.2mmol) in acetonitrile (3mL), add KOCN (0.4mmol), NCS (0.22mmol), and react at room temperature until benzenesulfonylhydrazone disappears completely (5-18 hours) , the product was extracted with ethyl acetate (200 mL), and the organic phase was washed with saturated Na 2 CO 3 Solution wash, saline wash, anhydrous MgSO 4 After drying, the solvent was evaporated under reduced pressure, and 2-toluenesulfonyl-1,2,4-triazol-3-one was isolated by column chromatography.

[0057] The spectral data are as follows:

[0058]

[0059] 43.5 mg, 69% yield. 1 H NMR (400 MHz, DMSO-d 6 )δ=12.85(brs,1H),7.93-7.81(m,4H),7.57-7.49(m,5H),2.40(s,3H); 13 C NMR (100 MHz, DMSO-d 6 )δ=152.3, 147.8, 145.9, 133.9, 131.6, 130.3, 129.1, 127.5, 125.8, 125.1, 21.1 ppm; HRMS(ESI):Calcd forC 15 H 14 N 3 O 3 S[M+H] + :316.0750,found:316.0753. ...

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 belongs to the field of organic chemistry, and relates to a preparation method of 1, 2, 4-triazole. The invention discloses a preparation method of 3-amino-1, 2, 4-triazole and 2-toluenesulfonyl-1, 2, 4-triazole-3-ketone, and particularly discloses a preparation method of 3-amino-1, 2, 4-triazole and 2-toluenesulfonyl-1, 2, 4-triazole-3-ketone. The preparation method comprises the following steps: preparing a series of 3-amino-1, 2, 4-triazole under the action of acid by taking benzenesulfonyl hydrazone and cyanamide as raw materials; a series of 2-toluenesulfonyl-1, 2, 4-triazole-3-ketone is prepared by taking benzenesulfonyl hydrazone and potassium cyanate as raw materials under the action of N-chlorosuccinimide.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a preparation method of 1,2,4-triazole. Background technique [0002] In recent years, a large number of studies and practices have shown that 1,2,4-triazole compounds have a wide range of biological activities, and 1,2,4-triazole compounds have been widely used in the field of medicine and pesticides. [0003] As shown in formula 1, the commonly used preparation method of 1,2,4-triazole compounds is as follows: chloromethylene amide and hydrazide are condensed to generate N-amidocarbazide, and N-amidocarbazide is cyclized and condensed in the molecule. Generate 1,2,4-triazole. The main disadvantages of this method include: (1) most of the reaction raw materials, chloromethylene amide and hydrazide, are not commercially available; (2) the reaction conditions are relatively harsh, for example, phosphorus oxychloride (POCl) is often used for the preparation of chloromethylene amide. ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/14C07D249/12C07D405/04C07D409/04
CPCC07D249/14C07D249/12C07D405/04C07D409/04
Inventor 唐萌魏泽洋
Owner LANZHOU UNIVERSITY
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