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A kind of preparation method of tricyclazole intermediate

An intermediate, tricyclazole technology, applied in the field of pesticide synthesis, can solve problems such as the limitation of reaction conditions of starting materials, and achieve the effect of simple process, less side reactions and easy separation

Active Publication Date: 2020-08-11
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, people have developed various methods for the synthesis of benzothiazole compounds, and in these methods, it is inevitable to use transition metals copper, palladium, iridium, silver as catalysts, and isothiocyanates can also be used. Synthesis of 4-methylbenzothiazol-2-amine by reaction with o-aminothiophenol under metal-free conditions, however, this method is limited by starting materials and harsh reaction conditions

Method used

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  • A kind of preparation method of tricyclazole intermediate

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Embodiment 1

[0024] 49.0 mg (0.5 mmol) 2-methyl-cyclohexane-1-one, 2 ml dimethylsulfoxide, 38.1 mg (0.5 mmol) thiourea, 38.1 mg (0.15 mmol) iodine, 475.6 mg (2.5 mmol) The p-toluenesulfonamide is put into the reactor successively, reacts in the air, at 70 o C under reflux for 24 h. After the reaction, add 20 ml of water to the system, extract 3 times with 20 ml of ethyl acetate, collect and combine the organic phases, add anhydrous sodium sulfate to dry, evaporate the solvent under reduced pressure and obtain the target product through column chromatography separation, the yield is 84%.

Embodiment 2

[0026] 49.0 mg (0.5 mmol) 2-methyl-cyclohexane-1-one, 2 ml dimethylsulfoxide, 38.1 mg (0.5 mmol) thiourea, 38.1 mg (0.15 mmol) iodine, 36.5 mg (1 mmol) The hydrochloric acid is put into the reactor successively, reacts in the air, at 70 o C under reflux for 24 h. After the reaction, add 20 ml of water to the system, extract 3 times with 20 ml of ethyl acetate, collect and combine the organic phases, add anhydrous sodium sulfate to dry, evaporate the solvent under reduced pressure and obtain the target product through column chromatography separation, the yield is 45%.

Embodiment 3

[0028] 49.0 mg (0.5 mmol) 2-methyl-cyclohexane-1-one, 2 ml dimethylsulfoxide, 38.1 mg (0.5 mmol) thiourea, 38.1 mg (0.15 mmol) iodine, 98.1 mg (0.5 mmol) The sulfuric acid is put into the reactor successively, reacts in the air, at 70 o C under reflux for 24 h. After the reaction, add 20 ml of water to the system, extract 3 times with 20 ml of ethyl acetate, collect and combine the organic phases, add anhydrous sodium sulfate to dry, evaporate the solvent under reduced pressure and obtain the target product through column chromatography separation, the yield is 36%.

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Abstract

The invention relates to a preparation method of a tricyclazole intermediate. According to the preparation method, 2-methyl-cyclohexan-1-one and thiourea are taken as reaction raw materials, environment-friendly, and safe and economic air is taken as an oxidant, so that the tricyclazole intermediate is prepared under an alkali catalyst system.

Description

technical field [0001] The invention (a preparation method of a tricyclazole intermediate) provides a good method for metal-free catalytic synthesis of 2-aminobenzothiazole, which belongs to the technical field of pesticide synthesis. Background technique [0002] Tricyclazole is a special fungicide for the control of rice blast, and 4-methylbenzothiazol-2-amine is an important intermediate for the synthesis of tricyclazole, which is also widely used in the synthesis of pesticides and medicines. So far, people have developed various methods for the synthesis of benzothiazole compounds, and in these methods, it is inevitable to use transition metals copper, palladium, iridium, silver as catalysts, and isothiocyanates can also be used. 4-Methylbenzothiazol-2-amine was synthesized by reaction with o-aminothiophenol under metal-free conditions. However, this method is limited by starting materials and harsh reaction conditions. So we invented to use 2-methyl-cyclohexane-1-one a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/82
Inventor 丁华平于国权孙霞林袁宇
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD