Green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol

An aminobenzene and arylmethyl technology, applied in the field of organic chemical synthesis, can solve problems such as large loss, and achieve the effects of high acid density, high catalytic yield and good catalytic activity

Inactive Publication Date: 2013-10-23
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the shortcoming that the amount of acidic ionic liquid catalyst used in the prior art and the amount of loss in recycling are very large, and provide a kind of reaction solvent with water, with the higher bissulfonate acid ion of acidity Liquid is used as a catalyst, a method for green catalytic synthesis of 2'-aminobenzothiazole-arylmethyl-2-naphthol with high product purity and yield

Method used

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  • Green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol
  • Green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol
  • Green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 1mmol of benzaldehyde, 1mmol of 2-aminobenzothiazole, 1mmol of β-naphthol, 3ml of water and 0.05mmol of bissulfonate acidic ionic liquid into a 25ml single-necked flask with a stirring bar and a reflux condenser. Stir vigorously at 80°C for 5 minutes, TLC (thin plate chromatography) detection, the raw material point disappears, cool to room temperature, and filter with suction, the obtained filter residue is recrystallized with 95% ethanol aqueous solution, and after vacuum drying, the pure product 2′-aminobenzothiazole is obtained -Phenylmethyl-2-naphthol, the yield is 94%. Add benzaldehyde, 2-aminobenzothiazole and β-naphthol directly to the filtrate for repeated use.

[0021] 2′-Aminobenzothiazole-phenylmethyl-2-naphthol: 1 H NMR (500MHz, DMSO-d 6 ): δ=6.97~7.86(m, 16H, ArH / CH), 8.80(s, 1H, -NH-), 10.13(s, 1H, -OH); IR(KBr): ν=3379, 1623, 1595 , 1544, 1518, 1445, 1332, 1270, 814, 750cm -1

Embodiment 2

[0023] Add 1mmol of 2-chlorobenzaldehyde, 1mmol of 2-aminobenzothiazole, 1mmol of β-naphthol, 5ml of water and 0.05mmol of bissulfonate acidic ionic liquid into a 25ml single-necked flask with a stirring bar and a reflux condenser. Vigorously stirred and reacted at 80°C for 4 minutes, detected by TLC (thin plate chromatography), the raw material point disappeared, cooled to room temperature, and filtered with suction, the obtained filter residue was recrystallized with 95% ethanol aqueous solution, and the pure product 2′-aminobenzothiazole was obtained after vacuum drying -(2-Chlorophenyl)methyl-2-naphthol, the yield is 95%. Directly add 2-chlorobenzaldehyde, 2-aminobenzothiazole and β-naphthol to the filtrate for repeated use.

[0024] 2'-Aminobenzothiazole-(2-chlorophenyl)methyl-2-naphthol: 1 H NMR (500MHz, DMSO-d 6 ): δ=6.96~8.04(m, 15H, ArH / CH), 8.82(s, 1H, -NH-), 9.91(s, 1H, -OH); IR(KBr): ν=3384, 1628, 1597 , 1543, 1440, 1319, 1271, 815, 754cm -1

Embodiment 3

[0026] Add 1mmol of 4-nitrobenzaldehyde, 1mmol of 2-aminobenzothiazole, 1mmol of β-naphthol, 5ml of water and 0.05mmol of bissulfonate acidic ionic liquid into a 25ml single-necked flask with a stirring bar and a reflux condenser. Vigorously stirred and reacted at 85°C for 3.5 minutes, detected by TLC (thin plate chromatography), the raw material point disappeared, cooled to room temperature, and filtered with suction, the obtained filter residue was recrystallized with 95% ethanol aqueous solution, and after vacuum drying, the pure product 2′-aminobenzo Thiazole-(4-nitrophenyl)methyl-2-naphthol, yield 96%. Directly add 4-nitrobenzaldehyde, 2-aminobenzothiazole and β-naphthol to the filtrate for repeated use.

[0027] 2'-Aminobenzothiazole-(4-nitrophenyl)methyl-2-naphthol: 1 H NMR (500MHz, DMSO-d 6 ): δ=7.06~8.14(m, 15H, ArH / CH), 8.92(s, 1H, -NH-), 10.21(s, 1H, -OH); IR(KBr): ν=3393, 1626, 1599 , 1534, 1443, 1349, 1270, 813, 753cm -1

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Abstract

The invention provides a green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol, belonging to the field of organic chemical synthesis. The method comprises the following steps: carrying out synthetic reaction, wherein the aromatic aldehyde:2-aminobenzothiazole:beta-naphthol mol ratio is 1:1:1, the bissulfonate acidic ion liquid catalyst accounts for 5-8 mol% of the aromatic aldehyde, the reaction temperature is 80-95 DEG C, the reaction time is 3-10 minutes, and the volume (ml) of the reaction solvent water is 3-5 times of the molar weight (mmol) of the aromatic aldehyde; and after the reaction is finished, cooling to room temperature, carrying out vacuum filtration, recrystallizing the filter residue with 95% ethanol, and carrying out vacuum drying to obtain the 2'-aminobenzothiazolyl-arylmethyl-2-naphthol.Compared with other synthesis methods, the invention has the characteristics of high catalytic activity, low catalyst consumption, recyclable catalyst, low environmental pollution in the whole process, simple and convenient after-treatment and the like.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a green catalytic method for synthesizing 2'-aminobenzothiazole-arylmethyl-2-naphthol. Background technique [0002] Heterocyclic compounds containing thiazole rings have broad-spectrum biological activities, can be used as local anesthetics, and have anticonvulsant, antiviral, antibacterial, insecticidal, anti-inflammatory and anti-allergic effects, and compounds containing aminothiazole rings have strong Physiologically active, it can be used to treat allergies, high blood pressure, osteoporosis, asthma, cancer, HIV virus, and also has a wide range of applications in cell biology. In addition, it is also a kind of good intermediate, and the amino functional group can undergo a series of reactions, and various compounds synthesized therefrom have a wide range of applications in medicine, pesticides, dyes, etc. Therefore, derivatives containing aminothiazole...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/82
CPCY02P20/584
Inventor 岳彩波储昭莲吴胜华
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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