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Synthetic method and application of N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide

A technology for the synthesis of benzothiazoles, which is applied in the chemical field, can solve the problems of difficult post-processing, low reaction yield, and difficult preparation, and achieve the effects of high yield, high detection sensitivity, and mild reaction conditions

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

AI Technical Summary

Problems solved by technology

However, these methods are limited in application due to the disadvantages of difficult preparation of raw materials, instability, low reaction yield, and difficult post-processing.

Method used

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  • Synthetic method and application of N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide
  • Synthetic method and application of N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide
  • Synthetic method and application of N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide

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Experimental program
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Effect test

Embodiment 1

[0013] 0.242g 2-(4-amino-2-hydroxyphenyl)benzothiazole (4-AHBA, 1mmol) and 0.198g carbonylimidazole (CDI, 1.2mmol) were added to 20mL toluene, in a dry and nitrogen-protected Stirring and reflux under the conditions for 8h, a large amount of light yellow solid appeared, and the reaction was stopped. The solvent was evaporated to dryness under reduced pressure, and the volume ratio of CH 2 Cl 2 :CH 3 The product was purified by silica gel column chromatography with OH=10:1 as the eluent to obtain a yellow solid substance with a yield of 90%.

Embodiment 2

[0015] Use a 100mL volumetric flask to prepare 5×10 -6 mol / L 4-DHBTU acetonitrile solution, then take 10mL of this solution and add it to seven 10mL volumetric flasks to prepare 2×10 -8 mol / L, 2×10 -7 mol / L, 2×10 -6 mol / L, 2×10 -5 mol / L, 2×10 -4 mol / L, 2×10 -3 mol / L, 2×10 -2 mol / L Zn 2+ Aqueous solution, 50μL each was added to seven 10mL 4-DHBTU acetonitrile solutions, so that Zn 2+ Concentrations were 1×10 -10 mol / L, 1×10 -9 mol / L, 1×10 -8 mol / L, 1×10 -7 mol / L, 1×10 -6 mol / L, 1×10 -5 mol / L, 1×10 -4 mol / L, measure the fluorescence spectrum after shaking well. Take the fluorescence peak area at 445nm as the ordinate, lg(c / 10 -11 ) is the working curve for the abscissa, and c is Zn 2+ Molar concentration. see working curve figure 1 , the two show an exponential relationship, the fluorescence peak area (A) and Zn 2+ The trend line equation for concentration c is:

[0016] A=2.1015×10 6 c 0.2481 (R 2 =0.9213)

[0017] Calculation example of spiked recovery ...

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Abstract

The invention relates to the field of chemistry, in particular to a synthetic method and application of N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide. The molecular structural formula of the N,N'-2-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide is shown at the right; and the synthetic method of the N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide comprises the step that 2-(4-amido-2-hydroxybenzene radical) benzothiazole, 4-AHBA for short, and carbonyl imidazole, CDI for short, are used as raw materials and react in toluene, benzene or xylene solvents to obtain the N, N'-bis-[3-hydroxy-4-(2-benzothiazole)phenyl] carbamide, for short 4-DHBTU. The reaction equation is shown at the right upper part. The invention has available reaction raw materials, mild reaction conditions and high yield; any other catalysts and (or) reaction auxiliary agents do not need to be added in the reaction process, the operation is simple and safe, the phenolic hydroxyl radical of the 4-AHBA does not need to be protected, and the recovery of a byproduct of the imidazole is convenient; and the 4-DHBTU is used as a fluorescent probe and used for the detection of Zn, the concentration lower limit of the Zn is measured and can reach 1*10mol / L, and Fe, Fe, Cd, Co, Mn, Cu, Ni, Ag, Sn, La and Pb all do not interfere the measurement of the concentration of the Zn.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a kind of excited state intramolecular proton transfer-urea derivative N, N'di-[3-hydroxyl-4-(2-benzothiazole)phenyl]urea (4-DHBTU) A new synthetic method; and the compound as a fluorescent probe in Zn 2+ application in detection. Background technique [0002] Excited-state intramolecular proton transfer (ESIPT)-urea derivatives are widely used in chemical sensors, laser dyes, and UV light stabilizers. Typical methods for the synthesis of urea derivatives include the addition of amines to isocyanates and the reaction of amines with carbamoyl halides. However, due to the disadvantages of difficult preparation of raw materials, instability, low reaction yield, and difficult post-processing, the application range of these methods is limited to a certain extent. Contents of the invention [0003] The object of the present invention is to provide a novel excited state intramolecular prot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
Inventor 尹静梅阳强贾颖萍崔颖娜周广运高大彬
Owner DALIAN UNIV
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