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Process of preparing 3-substituted 5-azo substituting group substituted-[1,3,4]-thia-dizole-2-thione

A kind of CH3CH2, methyl technology, applied in the direction of organic chemistry and so on

Inactive Publication Date: 2006-11-15
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is then to fill up the situation that the 3N-substituted-5-azo-substituted-[1,3,4]-thiadiazole-2-thione synthetic method is still blank, and proposes a method under mild conditions, A novel "one-pot" method for the high-yield preparation of 3N-substituted-5-azo-substituted-[1,3,4]-thiadiazole-2-thiones

Method used

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  • Process of preparing 3-substituted 5-azo substituting group substituted-[1,3,4]-thia-dizole-2-thione
  • Process of preparing 3-substituted 5-azo substituting group substituted-[1,3,4]-thia-dizole-2-thione
  • Process of preparing 3-substituted 5-azo substituting group substituted-[1,3,4]-thia-dizole-2-thione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Synthesis of 3N-naphthyl-5-naphthazo-[1,3,4]-thiadiazole-2-thione

[0016] The reaction equation is as follows:

[0017]

[0018] In a 250mL three-neck flask equipped with a thermometer, a reflux condenser and a stirring magnet, add 2.8g (8.0mmol) of di-α-naphthylthiocarbazone and 80mL of acetonitrile, and stir fully to dissolve the solid completely. After the system is deoxygenated, add 0.8g (10.5mmol) of carbon disulfide, and use 50% aqueous sodium hydroxide solution (8.0mmolNaOH is added in total) to adjust the reaction system to pH=13-14, control the system temperature at 45-50°C, and stir After 5 hours, the precipitate changed from red to brown, cooled to room temperature, filtered, washed with water, and dried below 100°C to obtain brown-yellow 3N-naphthyl-5-naphthazo-[1,3 ,4]-thiadiazole-2-thione crystals, yield 2.9g (yield 91.1%). The melting point is 206-207°C.

[0019] The physical and spectroscopic properties of the obtained compound are as f...

Embodiment 2

[0023] Example 2: Synthesis of 3N-p-chlorophenyl-5-p-chlorophenylazo-[1,3,4]-thiadiazole-2-thione

[0024] The reaction equation is as follows:

[0025]

[0026] In a 250mL three-necked flask equipped with a thermometer, a reflux condenser and a stirring magnet, add 2.6g (8.0mmol) of di-p-chlorophenylthiocarbazone and 80mL of acetonitrile, and stir fully to completely dissolve the solid. After deoxygenating the system, add 0.8g (10.5mmol) of carbon disulfide, and adjust the reaction system to pH=13-14 with 50% aqueous sodium hydroxide solution (8.0mmolNaOH added in total), control the system temperature at 45-50°C, and stir for 5h , generate a red precipitate, cool to room temperature, filter, wash the red precipitate with water, and dry below 100°C to obtain red 3N-p-chlorophenyl-5-p-chlorophenylazo-[1,3,4] - Thiadiazole-2-thione crystals, yield 2.6 g (yield 88.6%).

[0027] The physical and spectroscopic properties of the obtained compound are as follows:

[0028] Melt...

Embodiment 3

[0031] Example 3: Synthesis of 3N-o-benzyl-5-o-tolylazo-[1,3,4]-thiadiazole-2-thione

[0032] The reaction equation is as follows:

[0033]

[0034] In a 250mL three-necked flask equipped with a thermometer, a reflux condenser and a stirring magnet, add 2.25g (8.0mmol) o, o'xylene thiocarbazone and 80mL acetonitrile, and stir fully to dissolve the solid completely. After the system is deoxygenated, add 0.8g (10.5mmol) of carbon disulfide, and adjust the reaction system with 50% aqueous sodium hydroxide solution (8.0mmol NaOH is added) to make the pH=13-14, control the temperature of the system at 45-50°C, and stir After 12 hours, a red precipitate was formed, cooled to room temperature, filtered, washed with water, and dried below 100°C to obtain red 3N-o-benzyl-5-o-tolylazo-[1,3,4] - Thiadiazole-2-thione crystals, yield 2.35 g (yield 90.1%).

[0035] The physical and spectroscopic properties of the obtained compound are as follows:

[0036] Melting point: 139-140°C.

...

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Abstract

A process for preparing 3N-substituent-5-azo substituent substituted-[1,3,4]- thiadiazole-2-thione features the reaction between the monosubstituted or bisubstituted derivative of diphyenyl (or dinaphthyl) thiocarbazone and CO2 at a temp lower than 100 deg.C for the time shorter than 12 hr. Said product can be used for herbicide, bactericide, insecticide, dye, combustion inhibitor, additive of lubricating oil, antioxidant of rubber, etc.

Description

Technical field: [0001] The present invention relates to a novel process for the preparation of 3N-substituted-5-azo-substituted-[1,3,4]-thiadiazole-2-thiones. Background technique: [0002] Thiadiazole is an aromatic heterocyclic ring containing 2 nitrogen atoms and 1 sulfur atom. Its derivatives have strong biological activity and pharmacological activity, and have been widely used in pesticides, medicine, life science and chemical industry. In terms of pesticides, they have been greatly developed because of their biological activities such as herbicide, bactericide, insect repellent, plant growth regulator, and induction of plant disease resistance. In industry, thiadiazoles are widely used as dyes, flame retardants, lubricating oil additives, rubber antioxidants, stabilizers and photographic medicines. At present, people have synthesized mostly 2,3-substituted-[1,3,4]-thiadiazole, [1,2,3]-thiadiazole-4-thione derivatives, 2,4- Substituted-[1,3,4]-thiadiazole-5-thione a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/135C07C381/00
Inventor 建方方赵朴素许良忠
Owner QINGDAO UNIV OF SCI & TECH
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