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A kind of preparation method of amide compound

A technology for amide compounds and acid halides, which is applied in the field of preparation of amide compounds, can solve the problems of high price of reaction raw materials, many reaction three wastes, difficult treatment, etc., and achieves the effects of high bactericidal activity, reduced pollution, and increased safety.

Active Publication Date: 2021-10-29
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these two methods have key process problems such as expensive reaction raw materials, many reaction wastes and difficult treatment, and low yield.

Method used

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  • A kind of preparation method of amide compound
  • A kind of preparation method of amide compound
  • A kind of preparation method of amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Synthesis of 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one-O-benzoyl oxime (Compound III-68 in Table 1)

[0054] (1) Synthesis of 2-[(dimethylamino)methylene]-1,3-cyclohexanedione

[0055]

[0056] Add methanol (200.0g), dimethylamine solution (112.8g, 40%) and 1,3-cyclohexanedione (56.0g) into a three-necked flask with a mechanical stirring device, stir at room temperature for 30min, and cool to 0- At 10°C, formaldehyde solution (88.3g, 37%) was slowly added dropwise and stirred for 5h to obtain 2-[(dimethylamino)methylene]-1,3-cyclohexanedione, which was directly used in the next step.

[0057] (2) Synthesis of 2-methyl-1,3-cyclohexanedione

[0058]

[0059] The reaction solution from the previous step was transferred to an autoclave, a palladium carbon catalyst (5.6 g, 10%) was added, and the reaction was carried out at 2 MPa and 30° C. for 8 h. The reaction solution was taken out, the catalyst was filtered off, 200 g of water was added, methanol was distilled ...

Embodiment 2

[0070] Synthesis of 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one-O-pivaloyl oxime (Compound III-67 in Table 1)

[0071]

[0072] Add intermediate 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one oxime (21.1g), triethylamine (10.1g), toluene (200mL) to the reaction flask, Pivaloyl chloride (12.1 g) was added dropwise thereto, and stirred at room temperature for 3 h after dropping. The reaction solution was cooled to room temperature, and water (100 mL) was added, and stirred at this temperature for 30 min, and then the layers were separated. The oil layer was precipitated to obtain 28.4 g of intermediate 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one-O-pivaloyl oxime, yield: 96% (as 2-methyl Base-3-(2-pentyloxy)cyclohex-2-en-1-one oxime calculation).

Embodiment 3

[0074] Synthesis of 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one-O-acetyloxime (Compound III-65 in Table 1)

[0075]

[0076]Add intermediate 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one oxime (21.1g), triethylamine (10.1g), toluene (200mL) to the reaction flask, Acetyl chloride (7.9 g) was added dropwise thereto, and stirred at room temperature for 3 h after the drop was completed. The reaction solution was cooled to room temperature, and water (100 mL) was added, and stirred at this temperature for 30 min, and then the layers were separated. The oil layer was precipitated to obtain 24.8 g of the intermediate 2-methyl-3-(2-pentyloxy)cyclohex-2-en-1-one-O-acetyl oxime, yield: 98% (as 2-methyl- 3-(2-pentyloxy)cyclohex-2-en-1-one oxime).

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Abstract

A method for preparing benzamide compounds represented by the general formula (I), relates to the application of a carboxylic acid oxime ester compound as a fungicide. The reaction formula is as follows: the definitions of the substituents in the general formula can be found in the instructions. In the method, acid halide (II) and substituted carboxylic acid oxime ester (III) are condensed in a suitable solvent to prepare the amide compound as shown in general formula I. Carboxylate oxime esters can also be used as intermediates for the preparation of amide fungicides.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of amide compounds. Background technique [0002] Amide compounds have certain bactericidal activity, and CN104649973A discloses that the compound represented by the following general formula has good bactericidal activity against rice sheath blight. [0003] [0004] CN104649973A also discloses two preparation methods of amide compounds: reacting 3-difluoromethylpyrazole acid chloride compounds and substituted anilines under alkaline conditions to obtain the target product; Alkanes react under alkaline conditions to obtain the target product. However, these two methods have key technical problems such as expensive reaction raw materials, many reaction wastes and difficult treatment, and low yield. For a long time, technicians have been committed to continuously researching and developing new, more advanced, reasonable, and more environmental...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/75C07D231/14C07D231/16C07D241/24C07D213/81C07D277/587C07D285/06C07D333/38C07D307/68C07C225/20C07C221/00C07C49/403C07C45/61C07C49/753C07C45/64C07C251/42C07C249/08C07C251/68C07C249/12
CPCC07C45/61C07C45/64C07C221/00C07C225/20C07C233/75C07C249/08C07C249/12C07C251/68C07D213/81C07D231/14C07D231/16C07D241/24C07D277/587C07D285/06C07D307/68C07D333/38C07C2601/14C07C2601/16C07C49/403C07C49/753C07C251/42
Inventor 王刚王徵连伟祥郝泽生金守征关云飞杨辉斌李斌
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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