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Oxathiadiazole-2-oxide compound and preparation method thereof

A compound, potassium hydroxide technology, applied in the direction of organic chemistry, etc., can solve the problems such as no synthesis report

Inactive Publication Date: 2016-02-17
HARBIN INST OF TECH AT WEIHAI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The heterocyclic compound belongs to a new type of heterocyclic compound, and there is no report on its synthesis at home and abroad.

Method used

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  • Oxathiadiazole-2-oxide compound and preparation method thereof
  • Oxathiadiazole-2-oxide compound and preparation method thereof

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Embodiment Construction

[0012] Its reaction process is attached as follows figure 2 , where R 1 , R 2 For a hydrogen atom, an alkyl group, an aryl group, etc.

[0013] Specific preparation method example 1: 0.5 mmol 4-methyl-N'-(4-nitrobenzylidene) benzenesulfonyl hydrazide, 1 mmol N-chlorosuccinimide (additive), 0.5 mmol Molar potassium hydroxide (base) and 1 ml of nitromethane were mixed together and the reaction was stirred well at 0°C for 5 hours. After the reaction was completed, it was extracted, washed with organic solvent, concentrated, and purified by column chromatography to obtain 5-p-nitrophenyl-2-p-methylphenyl-1,2,3,4-oxathiadiazole-2-oxide The yield was 89%. Melting point is 100~101°C; H NMR spectrum 1 HNMR (400MHz, CDCl 3 )δ8.27(d,2H, J =8.7Hz)7.75(d,2H, J =8.3Hz)7.66(d,2H, J =8.7Hz)7.42(d,2H, J =8.2Hz)2.51(s,3H); C NMR 13 CNMR (100MHz, CDCl 3 )δ152.2, 149.6, 146.5, 135.6, 133.5, 130.0, 129.7, 128.6, 123.5, 21.8; infrared spectrum FTIR (film): 2925, 2854, 1595, 1525, 1377...

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Abstract

The invention relates to an oxathiadiazole-2-oxide compound and a preparation method thereof. The structural formula of the prepared oxathiadiazole-2-oxide compound is shown in a drawing, wherein R<1> and R<2> are hydrogen atoms, alkyl groups, aryl groups and the like. The preparation method comprises the following steps: sulfonylhydrazone, an additive and a base react at the temperature of 0-25 DEG C for 1-24 h; extraction, washing in an organic solvent and concentration are performed after reaction, column chromatographic purification is performed, the 1,2,3,4-oxathiadiazole-2-oxide compound is obtained, and the yield is 60%-95%, wherein the additive is N-iodosuccinimide, N-chlorosuccinimide, N-bromosuccinimide, iodine or other additives; the base is sodium carbonate, potassium carbonate, cesium carbonate, potassium hydroxide, sodium methoxide or other bases.

Description

technical field [0001] The invention relates to a class of oxathiadiazole-2-oxide compounds and a preparation method thereof. Background technique [0002] The present invention proposes and synthesizes oxathiadiazole-2-oxide compounds for the first time. The heterocyclic compound belongs to a new type of heterocyclic compound, and there is no report on its synthesis at home and abroad. The invention uses sulfonyl hydrazone compounds as raw materials to react with N-chlorosuccinimide under alkaline conditions to generate oxathiadiazole-2-oxide compounds. The invention has the advantages of simple operation, mild reaction conditions, simple synthesis process and purification method and high yield. Contents of the invention [0003] The object of the present invention is to provide a class of oxathiadiazole-2-oxide compounds. [0004] Another object of the present invention is to provide a method for preparing the above compound. [0005] In order to achieve the above ob...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D291/04
CPCC07D291/04
Inventor 吉元昭吴彦超李惠静
Owner HARBIN INST OF TECH AT WEIHAI
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