ChemicalBook CAS DataBase List METCONAZOLE

METCONAZOLE synthesis

10synthesis methods

Product Name:METCONAZOLE
CAS Number:125116-23-6
Molecular formula:C17H22ClN3O
Molecular Weight:319.83

Metconazole is commercially produced through a multi-step synthesis typical of triazole fungicides. The process begins with the construction of a substituted phenyl ring, which is then reacted with triazole intermediates to form the active molecule. Key steps include halogenation, alkylation, and condensation reactions under controlled conditions to ensure the correct stereochemistry and high purity of the final product.

Cyclopentanone, 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-

115851-28-0
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41253-21-8 Synthesis

41253-21-8
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$5.00/5g

25596-24-1 Synthesis

25596-24-1
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$6.00/10g

125116-23-6
138 suppliers
$85.00/100mg

Yield:125116-23-6 85%

Reaction Conditions:

with sodium hydroxide in 1-methyl-pyrrolidin-2-one at 110; for 5 h;Flow reactor;Inert atmosphere;Reagent/catalyst;Solvent;Temperature;

Steps:

1-2 A method for synthesizing metconazole, specifically:
In a 500 ml reaction flask equipped with a stirrer, a thermometer, a gas introduction tube and a distillation device,Add 50 grams (about 0.2 mole) of 2,2-dimethyl-5-(4-chlorobenzyl)cyclopentanone with a purity of 95% (the same below) by mass percentage,18.5 grams of sodium 1,2,4-triazole (about 0.2 mole), 5 grams (0.125 mole) of solid sodium hydroxide and 120 ml of N-methylpyrrolidone, stir and heat to 110°C; Start nitrogen bubbling (flow rate is about 30 liters/min), while bubbling nitrogen, add 38 grams (about 0.22 moles) of trimethylsulfoxonium bromide in batches for 4 hours.After the addition, bubbling was continued for 1 hour. HPLC analyzed that the molar percentage content of 2,2-dimethyl-5-(4-chlorobenzyl)cyclopentanone was less than 1%. The nitrogen bubbling was stopped and about 10 ml was evaporated. liquid. Concentrate under reduced pressure, add water and dichloroethane, extract the layers, concentrate, add methanol to recrystallize, and dry to obtain 54.5 g of metconazole as a white solid. The yield is 85%.

References:

Shanghai Heteng Fine Chemical Co., Ltd.;Shi Guancheng;Hu Haojie;Meng Haicheng CN111718304, 2020, A Location in patent:Paragraph 0031-0034

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288-88-0 Synthesis