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3-aminobenzo[d]isothiazole and derivatives thereof, and synthetic method thereof

A technology of isothiazole and aminobenzene, which is applied in the field of organic compounds and their synthesis, and achieves the effects of high product utilization value, expected market commercialization prospects, and simple reaction system

Active Publication Date: 2018-05-29
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no report on the direct synthesis of 3-aminobenzo[d]isothiazole from elemental sulfur

Method used

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  • 3-aminobenzo[d]isothiazole and derivatives thereof, and synthetic method thereof
  • 3-aminobenzo[d]isothiazole and derivatives thereof, and synthetic method thereof
  • 3-aminobenzo[d]isothiazole and derivatives thereof, and synthetic method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-29

[0085] Embodiment 1-29 all adopts the following steps to synthesize:

[0086] (1) Add alkali, benzamidine compound, elemental sulfur and organic solvent in reaction vessel;

[0087] (2) After fully mixing the reactants, heat them;

[0088] (3) purifying after the reaction to obtain the product;

[0089] Benzamidine compounds and reaction conditions are shown in the table.

[0090] Table: reactant, reaction conditions and productive rate of embodiment 1-29

[0091]

[0092]

[0093]

[0094] It should be pointed out that the reaction time is not only 36h, it can be very long, and here only 36h is set as the standard for comparing the yield.

[0095] The NMR and mass spectrometry data of the product of some embodiments are:

Embodiment 1

[0096] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0097] 1 H NMR (400MHz, DMSO-d 6 , ppm) δ9.60(s, 1H), 8.49(d, J=8.1Hz, 1H), 8.06(d, J=8.1Hz, 1H), 7.96(d, J=7.7Hz, 2H), 7.60( t, J=7.5Hz, 1H), 7.51(t, J=7.5Hz, 1H), 7.34(t, J=8.0Hz, 2H), 6.97(t, J=7.3Hz, 1H); 13 C NMR (100MHz, DMSO-d 6 , ppm) δ155.3, 149.9, 141.3, 128.8, 128.5, 127.5, 124.5, 122.8, 121.4, 120.6, 117.9; HRMS calcd.for: C 13 h 11 N 2 S[M+H] + 227.0638, found 227.0636.

Embodiment 2

[0098] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0099] 1 H NMR (400MHz, CDCl 3 , ppm) δ7.83(d, J=8.1Hz, 1H), 7.77(d, J=8.1Hz, 1H), 7.61(d, J=8.3Hz, 2H), 7.52(t, J=7.3Hz, 1H), 7.40(t, J=7.5Hz, 1H), 7.17(d, J=8.2Hz, 2H), 6.98(s, 1H), 2.33(s, 3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ154.7, 151.0, 137.7, 131.9, 129.6, 128.1, 127.0, 124.1, 120.8, 120.4, 118.5, 20.8; HRMS calcd.for: C 14 h 13 N 2 S[M+H] + 241.0794, found 241.0790.

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Abstract

The invention mainly relates to 3-aminobenzo[d]isothiazole and derivatives thereof and a synthetic method thereof. Benzamidine compounds and elemental sulfur are converted into 3-aminobenzo[d]isothiazole and the derivatives thereof only under the action of an alkali and in an air atmosphere without use of a catalyst during synthesis. The problems that a conventional synthetic method of a functionalized 3-aminobenzo[d]isothiazole compound has complex synthetic steps, requires a multistep synthesis process to complete, and also requires use of metal catalysts or peroxides, as well as has low yield or harsh reaction conditions are overcome. The synthetic method has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple experimental operation,wide sources of used materials, high yield, easy expanding of users and application, high utilization value of products, expectable prospects of commercialization of the market and the like.

Description

technical field [0001] The invention relates to an organic compound and a synthesis method thereof, in particular to 3-aminobenzo[d]isothiazole, derivatives and a synthesis method thereof. Background technique [0002] 3-Aminobenzo[d]isothiazole derivatives are characteristic motifs commonly found in natural products, pharmaceuticals, and many other bioactive products. However, there are very few effective methods for the synthesis of benzisothiazoles. Using 3-aminobenzo[d]isothiazolium chloride as raw material and 3-aminobenzo[d]isothiazole compounds as main raw materials, a series of benzisothiazolone derivatives were synthesized through S-N bonding reaction (methylthiosalicylate) between the SH and NH groups) using the hypervalent iodine reagent PIFA [(phenyliodide(III) bis(trifluoroacetate)] as the oxidizing agent. Recently, Yadav and co-workers Developed a method starting from 2-amino-N'-aryl-benzohydrazide and using Lawesson's reagent as a sulfur source. This method ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/04
CPCC07D275/04
Inventor 邓国军谢浩肖福红黄华文
Owner XIANGTAN UNIV