4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole and preparation method and application thereof

A technology of benziminothiazole and aminothiazole, which is applied in the field of new compounds and their preparation, and can solve the problems of no research reports on preparation methods and bactericidal activity

Inactive Publication Date: 2009-12-16
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benziminothiazole and ...

Method used

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  • 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole and preparation method and application thereof
  • 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole and preparation method and application thereof
  • 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-(2-hydroxybenzylimino)thiazole (Ia)

[0020]

[0021] (1) Preparation of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone

[0022]

[0023] Dissolve 0.05mol 3,3-dimethyl-1-chloro-2-butanone in 60mL ethyl acetate, add 0.05mmol 1,2,4-triazole, add potassium carbonate, reflux for 4.0h, post-treatment to obtain 3 , 3-Dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone, the yield is 80.6%.

[0024] (2) Preparation of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone

[0025]

[0026] 0.03mol 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone is dissolved in 45mL acetic acid, 0.03mol sodium acetate is added, 0.03mol bromine is added dropwise, at room temperature After stirring for 6.0 hours, 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-1-bromo-2-butanone was obtained by post-treatment, with a yield of 70.5%.

[0027] (3) Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-aminothiazole

[0028]

[0029] 0.01mol 3,3-dimethyl-1-(...

Embodiment 2

[0032] Example 2 Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-(2-hydroxy-3-bromobenzylimino)thiazole (Ib)

[0033]

[0034] (1) Preparation of 2-hydroxy-5-bromobenzaldehyde

[0035]

[0036] 7.5g (0.06mol) 2-hydroxybenzaldehyde is dissolved in 45mL ethanol, and 9.8g Br is added dropwise at 10~15℃ 2 (0.05mol) 45mL CCl 4 The solution was stirred for 0.5h and placed at room temperature for 1h. The precipitate was separated out, filtered with suction, and washed with 95% ethanol until the solution was colorless to obtain white needle-like crystals of 2-hydroxy-5-bromobenzaldehyde. The yield was 73%, and the melting point was 104-106°C.

[0037] (2) Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-(2-hydroxy-3-bromobenzylimino)thiazole (Ib)

[0038] Dissolve 1mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-aminothiazole in 20mL benzene, add 1mmol 2-hydroxy-5-bromobenzaldehyde, reflux for 1.5h, 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-(2-hydroxy-5-bromobenzylimino)thiazole was o...

Embodiment 3

[0039] Example 3 Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-(2-hydroxy-3,5-dibromobenzylimino)thiazole (Ic)

[0040]

[0041] (1) Preparation of 2-hydroxy-3,5-dibromobenzaldehyde

[0042]

[0043] Add 25.0g of 40% hydrobromic acid aqueous solution to the flask containing 40mL of glacial acetic acid and 7.5g (0.06mol) of 2-hydroxybenzaldehyde, stir at 30~40℃, slowly add NaClO dropwise 3 The solution reacted for 1.5h, producing a milky white precipitate. Add 30mL of absolute ethanol, warm it to dissolve completely, cool to precipitate white needle crystals, filter with suction, wash with a small amount of ethanol, and dry to obtain 2-hydroxy-3,5-dibromobenzaldehyde, yield 75.2%, melting point 83~85 ℃.

[0044] (2) Preparation of 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-(2-hydroxy-3,5-dibromobenzylimino)thiazole (Ic)

[0045] Dissolve 1mmol 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-aminothiazole in 20mL benzene, add 1mmol 2-hydroxy-3,5-dibromobenzaldehyde, and reflux 1.0h to o...

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Abstract

The invention discloses 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole (I) having the chemical structural formula shown rightwards. A method for preparing the 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole is as follows: the step of reflux reaction is carried out on the 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-aminothiazole and aryl aldehyde in benzene, thereby preparing the 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole. The 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzylimino thiazole can be used for preparing bactericide.

Description

Technical field [0001] The present invention relates to a new class of compounds and preparation methods and applications thereof, specifically 4-tert-butyl-5-(1,2,4-triazol-1-yl)-2-benzyliminothiazole and preparation methods thereof. application. Background technique [0002] Thiazole compounds have anticonvulsant, antiviral, bactericidal and insecticidal effects. Shao Ling et al. designed and synthesized 4-aryl-5-triazolylthiazole-2-imine compounds, and the biological activity test results showed that some compounds have fungicidal activity against Verticillium apple. Michael et al. studied 2-aminothiazole breast cancer drugs; Jiang Fengchao et al. designed and synthesized 4-arylthiazole-2-imine derivatives with inhibitory activity on apoptosis. Lin et al. reported that schiff base compounds have a selective inhibitory effect on COX-2. He Daohang et al. studied the synthesis and bactericidal activity of 4-aryl-2-(2-hydroxybenzylimino)thiazole; Hu Aixi et al. reported the synthe...

Claims

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Application Information

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IPC IPC(8): C07D417/04A01N43/78A01P3/00
Inventor 胡艾希覃智陈平叶姣
Owner HUNAN UNIV
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