Preparation method of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide

A technology of dioxide and benzoxane, applied in the field of organic chemical synthesis, can solve the problems of intolerable functional groups, long reaction period, complicated operation procedures, etc., and achieve the effects of easy preparation and mild reaction conditions.

Inactive Publication Date: 2018-08-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In this reaction, since the diazotization reaction involves the starting materials under acidic conditions, it is difficult to tolerate acid-sensitive functional groups. In addition, due to the step-by-step strategy, the reaction cycle is long and the operating procedures are cumbersome, which improves the efficiency of the reaction. The difficulty of industrial production of the reaction

Method used

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  • Preparation method of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide
  • Preparation method of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide
  • Preparation method of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Synthesis of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide:

[0032]

[0033] At room temperature, the raw material 2-aminobenzenesulfonamide (0.3mmol, 1equiv) and tertbutyl nitrite (0.45mmol, 1.5equiv) were added to the reaction vessel, and the reaction solvent acetonitrile (CH 3 CN, 2 mL), stirred at a reaction temperature of 25° C. until the end of the reaction (about 3 min), during which the reaction progress was monitored by thin-layer chromatography.

[0034] The mixture obtained after the reaction can be further separated and purified, for example: extraction, column chromatography, distillation, decantation, filtration, centrifugation, washing, evaporation, stripping, and adsorption to obtain a relatively pure final product.

[0035] Of course, if necessary, the mixture obtained after the reaction can also be pretreated, such as: concentration, extraction, vacuum distillation, and then introduced into other processes to produce other products, or directly introduce...

Embodiment 2

[0047] Amplified reaction of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide

[0048]

[0049] At room temperature, 2-aminobenzenesulfonamide (3mmol, 1equiv) and tertbutyl nitrite (4.5mmol, 1.5equiv) were added to the reaction vessel, and the reaction solvent CH 3 CN (20mL), stirred at a reaction temperature of 25°C for 15min; after the reaction was monitored by thin-layer chromatography, 10mL of ethyl acetate was added for extraction operation, then dried by adding anhydrous sodium sulfate, filtered after 5min, and the filter cake was washed with ethyl acetate (5mL×3 times), then spin off the solvent, and obtain the product after separation by column chromatography (eluent (volume ratio): petroleum ether: ethyl acetate=3:1), the product is a white solid, and the yield is 91%. .

[0050] As can be seen from the above Examples 1-2, when the preparation method of the present invention is adopted, 1,2,3-benzoxatriazine-1,1(2H)-dioxide can be obtained in a higher yield , providing a ...

Embodiment 3 to Embodiment 12

[0051] Example 3 to Example 12: Use of different reaction solvents

[0052] Except that the reaction solvent used is different, other operations of embodiment 3 to embodiment 12 are identical with embodiment 1, and the yield of reaction solvent used in each embodiment and corresponding product is shown in the table below:

[0053] Numbering

[0054]As can be seen from the table above, when using other organic solvents, such as the use of strong polar solvents 1,3-dimethyl-2-imidazolinone, N,N-dimethylformamide, N-methylpyrrolidone, Use non-polar solvent toluene, normal hexane, use weak coordination organic solvent 1,4-dioxane, the reaction can all take place, but the reaction effect in acetonitrile is better, and this has illustrated that the suitable selection of reaction solvent has great influence on the reaction. has a significant effect on the yield.

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Abstract

The invention discloses a preparation method of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide. The preparation method is characterized in that 2-aminobenzenesul fonamide and tert-butyl nitrite are taken asreaction materials and have a diazo-reaction in a reaction solvent to obtain 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide, and the reaction temperature is 0 DEG C to 50 DEG C. The preparation method has the beneficial effects that the reaction is efficient, the yield is high, the operation is convenient, and the postprocessing is simple; an oxidizing reagent or a catalyst are not required to be added;the reaction condition is mild, the reaction is carried out at a room temperature, the 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide is easy to prepare, and the reaction is green and economical.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide, and belongs to the technical field of organic chemical synthesis. Background technique [0002] 1,2,3,4-Benzoxatriazine-1,1(2H)-dioxide compounds are a kind of nitrogen-containing heterocyclic compounds, which have biological activities such as sterilization, anti-inflammation and inhibition of disordered growth of viruses , which are widely used in organic synthesis intermediates, dyes, preservatives, and are often found in the dominant structure of kinase inhibitors. [0003] At present, the method for the synthesis of 1,2,3,4-benzoxatriazine-1,1(2H)-dioxide compounds reported in the literature mainly utilizes 2-aminobenzenesulfonamide compounds as substrates, Diazobenzene is synthesized by diazotization reaction under acidic conditions, and then the pH value of the solution is adjusted so that an intramolecu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/15
CPCC07D285/15
Inventor 黄小波刘玮杨烨翡高文霞刘妙昌吴华悦李国兴吴祥庭
Owner WENZHOU UNIVERSITY
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