Method for preparing omega-(1H-1,2,4-triazol-1-yl)-arylethanone

A technology of hydroxyaryl ethyl ketone and aryl ethyl ketone, which is applied in the field of preparation of pesticide and pharmaceutical intermediate ω--aryl ethyl ketone, can solve the problems of low reaction yield and the like, achieves overcoming the low yield and is suitable for Wide range of effects with excellent yields

Active Publication Date: 2008-06-04
JIANGSU FENGDENG PESTICIDE
View PDF4 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In order to solve the problem of low reaction yield in the preparation of ω-(1H-1,2,4-triazol-1-yl)-arylethanone from ω-chloroarylethanone in the prior art, the present invention Provide a new method for preparing ω-(1H-1,2,4-triazol-1-yl)-arylethanone in high yield from ω-hydroxy arylethanone, the new preparation method is more Economical, more efficient, and suitable for large-scale 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
  • Method for preparing omega-(1H-1,2,4-triazol-1-yl)-arylethanone
  • Method for preparing omega-(1H-1,2,4-triazol-1-yl)-arylethanone
  • Method for preparing omega-(1H-1,2,4-triazol-1-yl)-arylethanone

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0046] The preparation method of the ω-(1H-1,2,4-triazol-1-yl)-arylethanone of the structure of formula (I) described in the present invention can also further make the halogen-substituted ω-(1H-1, 2,4-triazol-1-yl)-arylethanone is converted into aryloxy-substituted ω-(1H-1,2,4-triazol-1-yl)-arylethanone, namely the method It can further include:

[0047] (c) A preparation method of ω-(1H-1,2,4-triazol-1-yl)-arylethanone of structure of formula (Ib)

[0048]

[0049] In formula (Ib), R 1 Same as the definition in general formula (I), R 2 is phenoxy or is composed of halogen, alkyl, alkoxy, cyano, nitro or CF 3 Substituted phenoxy group; Make the omega-(1H-1,2,4-triazol-1-yl)-arylethanone represented by the structure of formula (Ia)

[0050]

[0051] In formula (Ia), R 1 Same as defined in general formula (I); R 2 Is a halogen; further etherification reaction with potassium phenate or sodium phenate in an organic solvent, converted into the corresponding ether compo...

Embodiment 1

[0064] Preparation of ω-formyloxy-2,4-dichloroacetophenone

[0065] Add 7.0g (0.12mol) of anhydrous sodium formate and 0.5g of tetrabutylammonium bromide into a solution consisting of 22.5g (0.1mol) of ω, 2,4-trichloroacetophenone and 100mL of toluene under stirring . The resulting mixture was heated to reflux, and continued to stir under reflux conditions, and the chromatographic trace was followed until the conversion of ω, 2,4-trichloroacetophenone was basically complete, which took about 5 hours. After the reaction was completed, it was washed with water, the organic layer was dried with anhydrous Na2SO4, and the solvent was precipitated under reduced pressure. The residue was 20.0 g, which was light brown viscous liquid, and the content of HPLC analysis was 96.1%. 1 H NMR: δ 5.37(s, 2H), 7.26(d, J=7.4Hz, 1H), 7.40(s, 1H), 7.72(d, J=7.4Hz, 1H), 8.01(s, 1H).

Embodiment 2

[0067] Preparation of ω-acetoxy-2,4-dichloroacetophenone

[0068] With reference to Example 1, 10.0g (0.15mol) anhydrous sodium acetate and 1.0g tetrabutylammonium bromide are added under stirring by 22.5g (0.1mol) omega, 2,4-trichloroacetophenone and In a solution composed of 100mL toluene. The obtained mixture was heated to reflux for 5 hours, and after treatment, 21.6 g of a brown viscous liquid was obtained, and the HPLC analysis content was 98.0%. EIMS (m / z, %): 250(M+4, 0.3), 248(M+2, 0.6), 246(M, 1.0), 186(2), 175(65), 173(100), 145 (21), 109(18), 77(17), 15(17).

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 provides a method to prepare omega-(1H-1, 2, 4- triazole-1-base) - arylethanone of formula (1) based on omega-hydroxyl arylethanone. The method comprises the steps that esterification reaction is done in the presence of alkali between the omega-hydroxyl arylethanone and at least one mole of sulfuryl chloride to generate corresponding arylacetyl methyl sulfonate and the arylacetyl methyl sulfonate in the presence of acid binding agent reacts with at least one mole of 1H-1, 2, 4- triazole or directly reacts with alkali metal salt of the 1H-1, 2, 4- triazole to generate the omega-(1H-1, 2, 4- triazole-1-base)- arylethanone, wherein, the Omega-(1H-1, 2, 4- triazole-1-base)- arylethanone substituted by aryloxy can be prepared by the etherification reaction of the omega-(1H-1, 2, 4- triazole-1-base)- arylethanone which can be substituted by halogen with potassium (sodium) phenate. The substituting groupR<1> and R<2> in the formula (I) structure are stated in the manual.

Description

technical field [0001] The invention relates to a method for preparing pesticide and pharmaceutical intermediate ω-(1H-1,2,4-triazol-1-yl)-arylethanone. Background technique [0002] ω-(1-H-1,2,4-triazol-1-yl)-arylethanone is an important intermediate of some triazole agricultural fungicides. For example, US4853399 (1989) reports that ω-(1H-1,2,4-triazol-1-yl)-2,4-disubstituted acetophenones are converted into corresponding ketal derivatives with fungicidal activity; EP065485 (1983) also involved the synthesis of difenoconazole (difenoconazole) and its homologues using a similar method. [0003] US4327104 (1982) ω-(1-H-1,2,4-triazol-1-yl)-substituted acetophenone is reduced into corresponding alcohol, then reacts with halogenated hydrocarbon to obtain a series of 1 with bactericidal activity -Substituted phenyl-2-(1H-1,2,4-triazol-1-yl)-ether derivatives. [0004] The ω-(1H-1,2,4-triazol-1-yl)-substituted acetophenone is also an intermediate of some medical antibacterial ...

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): C07D249/08
Inventor 纪立新耿荣伟
Owner JIANGSU FENGDENG PESTICIDE
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap