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Preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazole-5(4H)-one

A phenyl and methyl technology, applied in the field of fine chemical synthesis, can solve the problems of low equipment utilization rate, high condition requirements and high environmental protection requirements, and achieve the effects of high equipment utilization rate, simple process operation and no secondary pollution.

Active Publication Date: 2021-01-15
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] This route has the advantages of simple operation and stable process, but there are still deficiencies: (1) the quality requirements for sodium hypochlorite are high, and it needs to be used now; (2) the use of dangerous substance chlorine is involved, and the requirements for conditions are relatively high. High; (3) The amount of waste water is huge, and the requirements for environmental protection are high; (4) The utilization rate of equipment is low
[0008] CN1079963A discloses a method for synthesizing a triazolone ring with phenylhydrazine as a starting material, acetaldehyde, sodium cyanate and acetic acid as other raw materials, sodium hypochlorite as an oxidant, and tert-butanol as a solvent. Sodium hypochlorite is used for oxidation, and sodium hypochlorite must be made and used immediately, the amount of waste water is large, and the utilization rate of equipment is low
[0009] CN104672157A discloses a method of synthesizing 3-methyl-1-phenyl-1H at 70°C by using 5-methyl-2-phenyl-1,2,4-triazol-3-one and hydrogen peroxide as raw materials -1,2,4-triazol-5(4H)-ketone method, the product yield is 98.7%, but the method steps are long, the amount of waste water is large, and the utilization rate of equipment is low

Method used

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  • Preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazole-5(4H)-one

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Embodiment 1

[0025] A preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one of the present invention, comprising the following steps:

[0026] Add 17.7g (0.1mol) of 5-methyl-2-phenyl-1,2,4-triazol-3-one and 50g of tert-butanol into a four-necked flask with stirring, thermometer, condenser, and ventilation tube respectively Add 0.1 g of catalyst vanadium pentoxide under stirring, continue stirring, control the temperature of the system to 40°C to 50°C, and introduce air into the system, adjust the flow meter to the air flow rate of 20mL / min, and time the catalytic oxidation for 5 hours. The crude product of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one was obtained. After the catalytic oxidation reaction was completed, the reaction solution was concentrated, and the obtained solid was washed with water to obtain 16.2 g of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one with a content of 93.5 %, based on 5-methyl-2-phenyl-1,2,4-triazol-3-one, the yield is 86.6%.

Embodiment 2

[0028] A preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one of the present invention, comprising the following steps:

[0029] Add 17.7g (0.1mol) of 5-methyl-2-phenyl-1,2,4-triazol-3-one and 50g of tert-butanol into a four-necked flask with stirring, thermometer, condenser, and ventilation tube respectively In the process, add 0.26g of vanadium pentoxide catalyst under stirring, continue to stir, control the system temperature to 40°C-50°C, introduce air into the system, adjust the flow meter to the air flow rate of 20mL / min, time the catalytic oxidation for 5h, and catalyze Oxidation produced 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one crude product. After the catalytic oxidation reaction was completed, the reaction liquid was concentrated, and the obtained solid was washed with water to obtain 16.5 g of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one product with a content of 94.8% , based on 5-methyl-2-phenyl-1,2,4-triazol-3-one, the yield is 89.4%.

Embodiment 3

[0031] A preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one of the present invention, comprising the following steps:

[0032] Add 17.7g (0.1mol) of 5-methyl-2-phenyl-1,2,4-triazol-3-one and 50g of tert-butanol into a four-necked flask with stirring, thermometer, condenser, and ventilation tube respectively In the process, add 0.26 g of vanadium pentoxide catalyst under stirring, continue to stir, control the system temperature to 40 ° C ~ 50 ° C, introduce air into the system, adjust the flow meter to the air flow rate of 30 mL / min, and time the catalytic oxidation for 4 hours. Oxidation produced 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one crude product. After the catalytic oxidation reaction was completed, the reaction solution was concentrated, and the obtained solid was washed with water to obtain 16.3 g of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one product with a content of 94.6% , based on 5-methyl-2-phenyl-1,2,4-triazol-3-one, the yield is 88.1%.

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Abstract

The invention discloses a preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazole-5(4H)-one. The method comprises the following steps: carrying out a catalytic oxidation reaction at 40-50 DEG C by using 5-methyl-2-phenyl-1,2,4-triazole-3-one as a raw material, vanadium pentoxide as a catalyst, air as an oxidant and tert-butyl alcohol as a solvent to obtain the 3-methyl-1-phenyl-1H-1,2,4-triazole-5(4H)-one, wherein the content is 93-95%, and the yield is 85-90%. The method has the advantages of simple operation, easily available raw materials, less equipment investment, high equipment utilization rate, high safety and less three wastes, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemicals, and relates to a preparation method of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one, in particular to a catalytic oxidation Method for the synthesis of 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one. Background technique [0002] 3-methyl-1-phenyl-1H-1,2,4-triazol-5(4H)-one, English name: 3-methyl-1-phenyl-1H-1,2,4-triazol-5 (4H)-one is the main intermediate for the synthesis of the pesticide sulfentrazone, molecular formula: C 9 h 9 N 3 O, molecular weight: 175, molecular structure formula: [0003] [0004] Sulfentrazone is the first triazolinone herbicide launched by FMC. It was first reported at the Brighton Plant Protection Conference in England in 1991. It is a protoporphyrinogen oxidase inhibitor (PPO), which inhibits chlorophyll In the process of biosynthesis, protoporphyrinogen oxidase destroys the cell membrane, causing the leaves to dry up and die quickly. It ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12B01J23/22
CPCC07D249/12B01J23/22
Inventor 王胜得竺来发曾敬陈明吴曼刘伟曾雪云李敏尤瑶瑶
Owner 湖南海利常德农药化工有限公司