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Method for detecting secondary amine with thiobarbituric acid derivatives serving as probe molecules and preparation of thiobarbituric acid derivatives for detecting secondary amine

A technology of thiobarbituric acid and probe molecules, which is applied in chemical instruments and methods, analysis through chemical reactions of materials, measurement of color/spectral characteristics, etc., to achieve good selectivity, stable chemical properties, and reaction conditions mild effect

Inactive Publication Date: 2016-02-10
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The use of thiobarbituric acid derivatives in the detection of secondary amines has not yet been reported

Method used

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  • Method for detecting secondary amine with thiobarbituric acid derivatives serving as probe molecules and preparation of thiobarbituric acid derivatives for detecting secondary amine
  • Method for detecting secondary amine with thiobarbituric acid derivatives serving as probe molecules and preparation of thiobarbituric acid derivatives for detecting secondary amine
  • Method for detecting secondary amine with thiobarbituric acid derivatives serving as probe molecules and preparation of thiobarbituric acid derivatives for detecting secondary amine

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Experimental program
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Embodiment 1

[0047] Embodiment 1: Preparation of probe molecule 1,3-diphenyl 5 (2-furyl methylene) thiobarbituric acid (DPFTBA)

[0048] Aniline (11mmol), triethylamine (36.2mmol) and tetrahydrofuran 10mL were placed in a flask, stirred in an ice bath for 10min, and then carbon disulfide (11mmol) was added dropwise to the mixture within 30min; The solution was stirred and reacted at room temperature for 10 h; then cooled in an ice bath, TsCl (12.1 mmol) was slowly added, and stirred for 1 h to obtain 0.965 g of phenyl isothiocyanate. Dissolve 0.965g of phenyl isothiocyanate in dichloromethane, add 0.665g of aniline under ice-cooling condition, and stir for 45min. After the reaction is complete, filter; wash the filter cake several times with dichloromethane, and dry to obtain 1.497 g of N,N-diphenylthiourea. Mix 1.497g N,N-diphenylthiourea and dichloromethane in a round bottom flask, then add 7mmol malonyl chloride, heat to reflux for 1h, after the reaction is complete, remove the solvent...

Embodiment 2

[0051] Embodiment 2: Preparation of probe molecule 1,3-diethyl-5-(2-furyl methylene) thiobarbituric acid (DEFTBA)

[0052] Using steps similar to Example 1, 1,3-diethyl-2-thiobarbituric acid was obtained, which was mixed with ethanol and stirred evenly, and excess furan aldehyde and 0.5 mL pyridine were added, and stirred at room temperature for 2-3 h, Filtration, column chromatography separation, obtain target product 1,3-diethyl-5-(2-furyl methylene) thiobarbituric acid (1,3-diethyl-5-(2-furan-methylene )thiobarbituricacid) (structure shown in formula 6) 0.56g.

[0053] 1 HNMR (400MHz, CDCl 3 ): δppm = 8.73 (d, J = 3.9Hz, 1H), 8.46 (s, 1H), 7.91 (d, J = 1.2Hz, 1H), 6.78 (ddd, J = 3.8, 1.5, 0.7Hz, 1H) , 4.59 (qd, J=7.0, 4.6Hz, 4H), 1.33 (q, J=6.9Hz, 6H). (NMR image see Figure 10 )

[0054]

Embodiment 3

[0055] Embodiment 3: the application of the probe that detects secondary amines

[0056] The molecular probe (abbreviation) in Example 1 was dissolved in a mixed solvent of methanol containing 2% DMSO to prepare a probe solution with a concentration of 0.1 mg / mL. Add it into different solutions to be tested, shake it well at room temperature, let it stand in the dark for 0.5-1.0 h, and collect data with an ultraviolet-visible spectrophotometer.

[0057] figure 1 The colorimetric physical map shows the selectivity of its secondary amine compounds.

[0058] Figure 2 to Figure 5 The spectral properties of the probe molecule, the relationship between the concentration of the secondary amine and the absorbance, etc.

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Abstract

The invention discloses a method for detecting secondary amine with thiobarbituric acid derivatives (TBAs) serving as ultraviolet-visible light (UV-vis) spectrophotometric method probe molecules and preparation of the thiobarbituric acid derivatives for detecting secondary amine. The probe molecules are prepared from primary amine through a preparation line of a system. The probe molecules are provided with a furan ring (or thiophene ring) for recognizing secondary amine, an independent probe molecule solution is yellow, and along with addition of secondary amine, the solution becomes red from yellow. A molecular probe is high in selectivity and sensitivity to secondary amine, the response range to secondary amine is 100 micrometers to 400 micrometers, and the limit of detection (LOD) is 12 micrometers. Test paper can be prepared from the probe molecules, and qualitative detection on secondary amine can be achieved fast with low cost. The method can be widely applied to fast and sensitive detection such as online detection of secondary amine compounds, food analysis and environmental monitoring in the industrial process.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to the application of a probe molecule based on a furan ring opening mechanism in detecting secondary amine compounds and its preparation route. Background technique [0002] Secondary amine is a kind of organic amine, also known as secondary amine, the general formula is R 2 NH, and primary amine (RNH 2 ), tertiary amine (R 3 N), quaternary ammonium salt (R 4 N + x - ) together constitute the four major classes of organic amines. Secondary amines are the active groups of many natural products and bioactive molecules, and also the key active functional groups of many drugs such as tetracaine hydrochloride and epirenaline. Many foods contain secondary amines, such as pickled vegetables, sauerkraut, salted fish, bean paste, fried smoked fish, bacon, etc. Long-term consumption of foods containing high levels of secondary amines can lead to cancer. Therefo...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D405/06G01N21/31G01N21/33G01N21/78
Inventor 刘又年唐飞鹰臧启光邓留李娟
Owner CENT SOUTH UNIV
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