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Microwave synthesis method of benzaldoxime compounds

A technology of benzaldehyde oxime and microwave synthesis, which is applied in oxime preparation, organic chemistry and other directions to achieve the effects of high yield, convenient operation and short reaction time

Pending Publication Date: 2020-11-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Oximes are of great significance to the subsequent synthesis of drugs, but there are relatively few reports on benzaldoxime compounds

Method used

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  • Microwave synthesis method of benzaldoxime compounds
  • Microwave synthesis method of benzaldoxime compounds
  • Microwave synthesis method of benzaldoxime compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The preferred of embodiment 1 experimental method

[0018] Dissolve the substituted benzaldehyde and the basic compound in the solvent, add hydroxylamine hydrochloride, stir at room temperature under the reaction calciner or react at room temperature in a microwave reactor, follow the reaction by TLC, filter after the reaction is completed, spin to dry the solvent, and use ethyl acetate Mix and extract with water 1:1, separate the organic phase and dry it with anhydrous sodium sulfate, filter and precipitate to obtain benzaldoxime derivatives, and optimize the reaction conditions, as shown in Table 1.

[0019] The comparison of productive rate under table 1 different operating techniques

[0020]

[0021]

[0022] As can be seen from Table 1, conventional method ethanol is made solvent normal temperature stirring 1-3 hour reaction is completed, and methanol is made solvent and needs room temperature stirring 3-4 hour reaction is completed, and ethanol is made solv...

Embodiment 2

[0023] The preparation of embodiment 2 benzaldoxime

[0024] Benzaldehyde (0.10g, 0.94mmol), hydroxylamine hydrochloride (0.08g, 1.16mmol), anhydrous sodium carbonate (0.12g, 1.17mmol) were dissolved in ethanol (3ml), placed in a microwave reactor and heated at 90°C, Reacted under the condition of 300W for 5 minutes, the reaction was completed, and the conversion rate detected by gas chromatography was 90.125%. The solvent was spin-dried, mixed with ethyl acetate (10ml) and water (10ml) for extraction, and the organic phase was separated and dried with anhydrous sodium sulfate. Filtration and precipitation to obtain the benzaldoxime represented by formula (A1).

[0025]

[0026] Benzaldehyde oxime: pale yellow oil, microwave yield 88.9%; 1 HNMR (CDCl 3 , 500MHz), δ: 8.93 (s, 1H, OH), 8.17 (s, 1H, CH), 7.56-7.24 (m, 5H, ph).

Embodiment 3

[0027] The preparation of embodiment 3 o-methylbenzaldehyde oxime

[0028] Dissolve o-tolualdehyde (0.10g, 0.83mmol), hydroxylamine hydrochloride (0.07g, 1.01mmol), anhydrous sodium carbonate (0.11g, 1.07mmol) in ethanol (3ml), place in a microwave reactor and React for 5 minutes under the conditions of 90°C and 300W. After the reaction is completed, the conversion rate detected by gas chromatography is 88.461%. The solvent is spin-dried, extracted with ethyl acetate (10ml) and water (10ml), and the organic phase is separated and washed with anhydrous sulfuric acid. Sodium drying, filtration, precipitation, the o-tolualdehyde oxime shown in formula (A2) is obtained.

[0029]

[0030] o-Tolualdehyde oxime: colorless oil, microwave yield 85.8%; 1 HNMR (CDCl 3 ,500MHz), δ:8.43(s,1H,CH),7.69-7.67(m,1H,ph),7.59(s,1H,OH),7.31-7.28(m,1H,ph),7.24-7.20( m,2H,ph),2.45(s,3H,CH 3 ).

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Abstract

The invention discloses a microwave synthesis method of benzaldoxime compounds. The method comprises the following steps: dissolving a substituted benzaldehyde, hydroxylamine hydrochloride and an alkaline compound in an organic solvent, placing the formed solution in a microwave reaction kettle for a reaction, spin-drying the solvent after the reaction is finished, conducting mixed extraction withethyl acetate and water, separating an organic phase, carrying out drying with anhydrous sodium sulfate, and successively performing filtering and desolventizing to obtain a benzaldoxime compound. Based on the structure of the substituted benzaldehyde, the substituted benzaldoxime compound is obtained by reacting the aldehyde with hydroxylamine hydrochloride in the microwave reaction kettle. Themethod is simple in process, convenient to operate, short in reaction time and high in yield, meets the requirement for environment friendliness and improves economic benefits.

Description

technical field [0001] The invention relates to a microwave synthesis method of benzaldoxime compounds. Background technique [0002] As an effective substance for purifying carbonyl compounds, oxime is widely used in the synthesis of various nitrogen-containing medicines and pesticide intermediates, such as oxacillin and pyrethroids, due to its nucleophilicity. Oxime compounds have excellent Insecticidal, bactericidal, herbicidal, and anti-plant virus activities, many varieties also have the advantages of low toxicity and low residue, and their downstream products oxime ether and oxime ester derivatives also have excellent insecticidal, bactericidal, acaricidal, and herbicidal activities. Since Tranid, the first oxime ester pesticide, was developed in 1963, carbamate oxime ester insecticides such as Aldicard and Methomyl, and Phoxime have been successively developed. ), methyl phoxim (Phoxime-methyl) and other oxime phosphate insecticides, and the insecticide phosphacarb (...

Claims

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Application Information

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IPC IPC(8): C07C249/08C07C251/48
CPCC07C249/08C07C251/48
Inventor 陈委婷翁建全谭成侠刘幸海
Owner ZHEJIANG UNIV OF TECH
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