Preparation method for triticonazole intermediate

An intermediate, the technology of Fenbenazole, applied in the direction of condensation preparation of carbonyl compounds, organic chemistry, etc., can solve problems such as difficult production, and achieve the effects of improving purity, controlling impurity content, and low cost

Active Publication Date: 2014-11-05
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Abstract
  • Description
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Problems solved by technology

And fenconazole intermediate 5-(4-chlorobenzylidene)-2,2-dimethylcyclopentanone is a kind of compound that is not easy to produce industrially, and the synthesis of this intermediate in domestic and foreign patents or literature is scarce at present. It has been reported, and the product of Fenconazole is still blank in China

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  • Preparation method for triticonazole intermediate
  • Preparation method for triticonazole intermediate
  • Preparation method for triticonazole intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0039] This example provides a kind of preparation method of 5-(4-chlorobenzylidene)-2,2-dimethylcyclopentanone, which comprises the steps:

[0040] (1) Oximation reaction

[0041] Add 10.9 g of cyclopentanone, 12.8 g of morpholine, 0.2 g of p-toluenesulfonic acid, and 50 ml of toluene into a 250 ml dry three-necked flask, and react at 70° C. for 5 hours. Follow the reaction by TLC until the cyclopentanone is completely reacted. Wash with water, separate layers, and desolventize the toluene layer to 100°C to obtain 19.5 g of residue, which is Intermediate I. Purity (HPLC) 98.9%, yield: 98.2% (calculated as cyclopentanone).

[0042] (2) Condensation reaction

[0043] Add 19.5 grams of intermediate I and 18 grams of p-chlorobenzaldehyde in a 250 ml dry three-necked flask, 65 ml of toluene, and react at 60°C for 2 hours, follow the reaction by TLC until the intermediate I completely disappears, distill the toluene under reduced pressure to an internal temperature of 80 °C, 33 ...

Embodiment 2

[0049] This example provides a kind of preparation method of 5-(4-chlorobenzylidene)-2,2-dimethylcyclopentanone, which comprises the steps:

[0050] (1) Oximation reaction

[0051] Add 10.9 g of cyclopentanone, 12.8 g of morpholine, 0.2 g of anhydrous aluminum sulfate, and 50 ml of cyclohexane into a 250 ml dry three-necked flask, and react under reflux for 5 hours, and follow the reaction by TLC until the cyclopentanone is completely reacted. Washed with water, separated into layers, and the cyclohexane layer was precipitated under negative pressure to an internal temperature of 80° C. to obtain 18.8 g of a residue, which is Intermediate I. HPLC purity: 97.3%, yield: 92.2% (calculated as cyclopentanone).

[0052] (2) Condensation reaction

[0053] Add 18.8 g of intermediate I, 17.4 g of p-chlorobenzaldehyde, and 95 g of methylcyclohexane into a 250 ml dry three-necked flask, react at 50° C. for 2 hours, follow the reaction by TLC until intermediate I completely disappears. ...

Embodiment 3

[0059] Add 10.9 g of cyclopentanone, 12.8 g of morpholine, 0.2 g of anhydrous aluminum sulfate, and 50 ml of cyclohexane into a 250 ml dry three-necked flask, and react at 40° C. for 5 hours. Follow the reaction by TLC until the cyclopentanone is completely reacted. Washed with water, separated into layers, and the cyclohexane layer was precipitated under negative pressure to an internal temperature of 80° C. to obtain 18.9 g of a residue, which is Intermediate I. HPLC purity: 96%, yield: 91.4% (calculated as cyclopentanone).

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Abstract

The invention relates to a preparation method for a triticonazole intermediate 5-(4-chlorobenzylidene)-2,2-dimethylcyclopentanone. The preparation method comprises: (1) performing an oximation reaction on cyclopentanone and morpholine in an organic solvent in the presence of p-methylbenzene sulfonic acid at a temperature of 40-80 DEG C, so as to generate an intermediate I; (2) performing a condensation reaction on the intermediate I and p-chlorobenzaldehyde in a solvent at a temperature of 40-80 DEG C, so as to generate an intermediate II; (3) hydrolyzing the intermediate II under an acidic condition to generate an intermediate III; and (4) performing a methylation reaction on the intermediate III and a halogenated methane in a polar solvent in the presence of a strong base at a temperature of 40-80 DEG C, so as to generate 5-(4-chlorobenzylidene)-2,2-dimethylcyclopentanone. The technology is relatively simple, is capable of effectively controlling the impurity content in the product a improving the product impurity, and is low in cost and beneficial for realizing nationalization of triticonazole.

Description

technical field [0001] The present invention relates to a kind of preparation method of agricultural fungicide fenconazole and its intermediate. Background technique [0002] Triticonazole is a triazole fungicide developed and developed by Bayer. Chemical name (RS)-(E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1(1H-1,2,4-triazol-1-ylmethyl)cyclopenta Alcohol, its structural formula is as follows: [0003] [0004] Mechanism and characteristics of Fenconazole C-14 demethylase inhibitor in sterol biosynthesis, mainly used as seed treatment agent. Suitable crops are cereal crops, leguminous crops, fruit trees such as apples, etc. It is safe and has no phytotoxicity to crops under the recommended dose for crop safety. Control targets include Fusarium (mold) genus, Puccinia spp., Sclerotia spp., Smut, Tilletia spp., Powdery mildew spp., Septoria rotundum, Septoria spp. Diseases caused by genus such as powdery mildew, rust, black fish disease, net spot and so on. The method of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/697C07C45/45C07D249/08
CPCC07C45/45C07D249/08C07C49/697
Inventor 闫立单顾松山余强徐洪喜
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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