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4/5-Methyl-1,2,3-thiadiazolecarboxylic acid derivative and preparation method

A technology for thiadiazole and its derivatives, which is applied in the field of 4/5-methyl-1,2,3-thiadiazole formic acid derivatives and its preparation, and can solve the problems of few research reports on synthesis and biological activity

Inactive Publication Date: 2014-10-01
TIANJIN UNIV OF COMMERCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are relatively few reports on the synthesis and biological activity of 1,2,3-thiadiazole derivatives

Method used

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  • 4/5-Methyl-1,2,3-thiadiazolecarboxylic acid derivative and preparation method

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Experimental program
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Embodiment 1

[0056] Preparation of intermediate 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride:

[0057] At room temperature, add 30.0g (0.21mmol) 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 200mL anhydrous toluene and 49.5g (0.42mmol) thionyl chloride to a 500mL three-necked flask , slowly raised the temperature to 85°C, kept at 85°C for 6 hours, cooled to room temperature and filtered, the filtrate was evaporated under reduced pressure to remove excess thionyl chloride and desolventized to obtain the intermediate 4-methyl-1,2,3-thio Oxadiazole-5-carbonyl chloride.

Embodiment 2

[0059] Preparation of intermediate 5-methyl-1,2,3-thiadiazole-4-carbonyl chloride:

[0060] At room temperature, add 30.0g (0.21mmol) 5-methyl-1,2,3-thiadiazole-4-carboxylic acid, 200mL anhydrous toluene and 49.5g (0.42mmol) thionyl chloride to a 500mL three-necked flask , slowly raised the temperature to 85°C, kept at 85°C for 6 hours, cooled to room temperature and filtered, the filtrate was evaporated under reduced pressure to remove excess thionyl chloride and precipitated to obtain the intermediate 5-methyl-1,2,3-thio Oxadiazole-4-carbonyl chloride.

Embodiment 3

[0062] Compound Ⅲ-1: Synthesis and structure identification of 1-(2-aminoethyl)amino-9,10-anthraquinone-4-methyl-1,2,3-thiadiazole-5-carboxamide:

[0063] At room temperature, in a 50mL round bottom flask, add 0.17g (0.63mmol) of 1-(2-aminoethyl)amino-9,10-anthraquinone, 0.13g (0.94mmol) of triethylamine and 4-dimethyl Aminopyridine 3.8mg (0.03mmol), use anhydrous dichloromethane 30mL as solvent, stir to dissolve. Then slowly add 1.26 mmol of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride, and react at room temperature for 2 hours after the addition is complete. Then the reaction solution was concentrated to dryness, added 20 mL of 2N hydrochloric acid solution, transferred to a separatory funnel, extracted with dichloromethane and discarded the water layer, and then the obtained dichloromethane solution was fully washed with 20 mL of 5% sodium hydroxide solution. Discard the water layer and flocs, then fully wash the obtained dichloromethane solution with saturated sodium ch...

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Abstract

The invention discloses a 4 / 5-methyl-1, 2, 3-thiadiazole formic acid derivative and a preparation method and an application thereof. An aromatic nucleus structure is introduced into a 1, 2, 3-thiadiazole compound molecule to synthesize the 1, 2, 3-thiadiazole formic acid derivative containing aromatic nucleus components of porphyrin, anthraquinone and tertiary aromatic amine. The derivative has the chemical structural general formula represented as follows: when X is NH, R is 1-(2-amino ethyl group) amino group-9, 10-anthraquinone or 5-(4- aminophenyl)-10, 15, 20-triphenyl porphyrin group; and when the X is O, the R is N, N-2 (4-methyl phenyl) aminobenzene formoxime group. The 4 / 5-methyl-1, 2, 3-thiadiazole formic acid derivative is used in bacteriacide.

Description

technical field [0001] The invention relates to a thiadiazole-containing compound, in particular to a 4 / 5-methyl-1,2,3-thiadiazole formic acid derivative, a preparation method and use thereof. Background technique [0002] Thiadiazoles and aromatic heterocyclic compounds have a wide range of biological activities and become research hotspots. 1,2,3-thiadiazole compounds have the same wide range as 1,3,4-thiadiazole compounds, 1,2,5-thiadiazole compounds and Biological activity, related patents and literature summary see the monograph of Bakulev, et al. Newyork: John Wiley & Sons, Inc, 2004. In the past ten years, research on thiadiazole group-containing compounds with antibacterial activity has found that the introduction of aromatic structural groups into thiadiazole molecules can greatly improve their antibacterial activity. At present, the commercialized 1,2,3-thiadiazole derivative fungicide is thiazinil (3'-chloro-4,4'-dimethyl-1,2,3 -thiadiazole-5-carboxanilide, TDL...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/06C07D487/22A01N43/90A01N43/828A01P3/00
Inventor 刘立增李岳东王盾毛武涛
Owner TIANJIN UNIV OF COMMERCE