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A kind of method of synthesizing 2-substituted benzothiazole derivatives

A technology of benzothiazoles and benzothiazoles, which is applied in the field of synthesizing 2-substituted benzothiazole derivatives, can solve the problems of high raw material preparation costs, instability of o-aminothiophenol, long synthesis steps, etc. Short, low-cost, easy-to-operate effect

Active Publication Date: 2017-05-10
INNER MONGOLIA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, o-aminothiophenol, N-aryl thioamide or thiourea, and o-haloaniline are mainly used as raw materials to synthesize benzothiazole derivatives; wherein o-haloaniline and N-aryl thioamide or thiourea The synthesis steps are relatively long and the cost of raw material preparation is relatively high
Therefore, o-aminothiophenol is usually used to react with aldehydes to synthesize benzothiazole derivatives, but o-aminothiophenol is unstable and is easily oxidized and dimerized to form disulfides
In the prior art, there are few reports on a new method for preparing benzothiazole derivatives by reacting stable and easily available disulfides with aldehydes

Method used

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  • A kind of method of synthesizing 2-substituted benzothiazole derivatives
  • A kind of method of synthesizing 2-substituted benzothiazole derivatives
  • A kind of method of synthesizing 2-substituted benzothiazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 takes benzaldehyde as raw material synthesis 2-phenylbenzothiazole

[0023] (1) Synthesis of 2-phenylbenzothiazole

[0024] a: disulfide: aldehyde: Na 2 S·9H 2 O: NaHCO 3 =1:2:0.2:0.2

[0025] Add 0.40mmol of 2,2'-dithiodiphenylamine, 0.80mmol of benzaldehyde, 0.08mmol of Na to the parallel synthesizer reaction tube 2 S·9H 2 O and 0.08 mmol NaHCO 3 , and then added 3mL DMF as a reaction solvent, stirred and reacted at 100°C for 8 hours, LC detection found that the reaction of the disulfide raw material was complete, cooled to room temperature, and used a rotary evaporator to remove the solvent under reduced pressure to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) using petroleum ether and ethyl acetate as the eluent, using gradient elution, to obtain 155 mg of white powder 2-phenylbenzothiazole with a purity greater than 99%. Isolated in 90% yield, melting point 107-108°C.

[0026] b: dis...

Embodiment 2

[0035] Embodiment 2 takes benzaldehyde as raw material synthesis 2-phenylbenzothiazole (feeding amount is 15 times of embodiment 1)

[0036] (1) Synthesis of 2-phenylbenzothiazole

[0037]Add 6mmol of 2,2'-dithiodianiline, 12mmol of benzaldehyde, 3mmol of Na in a 250mL three-necked flask 2 S·9H 2 O and 3 mmol NaHCO 3 , and then added 20 mL of DMF as a reaction solvent, stirred and reacted at 100 ° C for 8 hours, LC detection found that the reaction of the disulfide raw material was complete, cooled to room temperature, and used a rotary evaporator to remove the solvent under reduced pressure to obtain a crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) with petroleum ether and ethyl acetate as eluent, and gradient elution was used to obtain 1.95 g of white powder 2-phenylbenzothiazole with a purity greater than 99%. , with an isolated yield of 80% and a melting point of 107-108°C.

[0038] (2) For the identification of the st...

Embodiment 3

[0039] Embodiment 3 takes p-chlorobenzaldehyde as raw material synthesis 2-(4-chlorophenyl) benzothiazole

[0040] (1) Synthesis of 2-(4-chlorophenyl)benzothiazole

[0041] Add 0.40mmol of 2,2'-dithiodiphenylamine, 0.80mmol of p-chlorobenzaldehyde, 0.08mmol of Na 2 S·9H 2 O and 0.08mmol of AcOH, then add 3mL of DMF as a reaction solvent, and stir and react at 100°C for 8 hours. LC detection shows that the reaction of the disulfide raw material is complete. Cool to room temperature, and use a rotary evaporator to remove the solvent under reduced pressure to obtain crude product. The crude product was separated by column chromatography (200-300 mesh silica gel) using petroleum ether and ethyl acetate as eluent, and gradient elution was used to obtain white powder 2-(4-chlorophenyl) with a purity greater than 99%. Benzothiazole 167mg, isolated yield 85%, melting point 112-113°C.

[0042] (2) Identification of the structure of 2-(4-chlorophenyl)benzothiazole

[0043]

[00...

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Abstract

The invention discloses a method of synthesizing a 2-substituted benzothiazole-type derivative, wherein the method includes a step of synthesizing the 2-substituted benzothiazole-type derivative with an aldehyde and a disulphide as raw materials under a combined effect of at least one from NaHCO3 and AcOH with a metal sulfide. The particular reaction is represented as follows, wherein the R comprises one or more from a hydrogen atom, a C1-C4 alkyl, a fluorine atom, a chlorine atom, a bromine atom, an amino group, a cyan group and a nitryl group; the R' substituent group comprises at least one from a C1-C6 alkyl, a furan group, a thienyl group, a pyrryl group, a pridyl group and a substituted phenyl group. The method employs the raw material being stable and easy to obtain, and can quickly and conveniently synthesize the 2-substituted benzothiazole-type derivative at a high production yield.

Description

technical field [0001] The invention relates to the technical fields of industry, materials and medicine, in particular to a method for synthesizing 2-substituted benzothiazole derivatives. Background technique [0002] 2-Substituted benzothiazole derivatives are an extremely important class of heterocyclic compounds, which have broad application prospects in the fields of industry, pesticides, medicine, and materials. In industrial production, it is a widely used chemical raw material, which can be used as a plastic dye and a raw material for making cosmetics; in pesticides and medicines, it is an intermediate with superior performance, which is more and more widely used The introduction of benzothiazole groups into the structures of different compounds plays a certain structural modification role and can produce a series of biologically active compounds; in the field of materials, the ligands of benzothiazole derivatives form complexes with metals, It has good electron tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/54C07D333/60C07D333/56C07D417/04
CPCC07D277/66C07D417/04
Inventor 竺宁刘波洪海龙韩利民索全伶
Owner INNER MONGOLIA UNIV OF TECH