Phenothiazine compound and preparation method and application thereof

A compound and phenothiazine technology, applied in the field of functional compound synthesis, can solve the problems of insufficient phosgene selectivity, complicated fluorescent probe synthesis, low yield, etc., achieving stable structure, high preparation yield, and improved reaction selectivity Effect

Active Publication Date: 2019-10-11
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these fluorescent probes still face problems such as complex synthesis, low yield, and insufficient selectivity to phosgene.

Method used

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  • Phenothiazine compound and preparation method and application thereof
  • Phenothiazine compound and preparation method and application thereof
  • Phenothiazine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The synthesis of embodiment 1 intermediate 1

[0035]

[0036] Iodoethane (3.9g, 25mmol) and 2-methoxyphenothiazine (2.29g, 10mmol) were dissolved in 20mL of dimethyl sulfoxide, then NaOH (0.8g, 20mmol) was added, and the temperature was raised to 65°C for 15 Hour. After the reaction was completed, cool to room temperature, add 300mL of water, add dichloromethane (50mL×2) for extraction, wash with saturated brine (50mL×2), dry over anhydrous sodium sulfate, then remove the solvent under reduced pressure, and use the obtained residue with Separation on a 200-300 mesh silica gel column gave a white solid (2.3 g, 89.5%).

[0037] 1 H NMR (600MHz, DMSO-d 6 )δ7.14 (ddd, J=8.4, 7.2, 1.4Hz, 1H), 7.08 (dd, J=7.6, 1.7Hz, 1H), 7.02–6.94 (m, 2H), 6.92–6.86 (m, 1H) ,6.51(d,J=7.6Hz,2H),3.87(q,J=6.9Hz,2H),3.70(s,3H),1.25(t,J=6.9Hz,3H).

Embodiment 2

[0038] The synthesis of embodiment 2 compound 2

[0039]

[0040] Under nitrogen protection, 1.7mL DMF was added dropwise in phosphorus oxychloride (1mL) under ice bath, after stirring for 15 minutes, DMF solution (7.5mL) of Intermediate 1 (2.57g, 10mmol) was added dropwise to in the above reaction solution. After the dropwise addition, the temperature was raised to 60°C to continue the reaction for 4 hours, then the reaction solution was poured into ice water, stirred for a while, and saturated NaHCO 3 The solution was neutralized to neutral pH, then dichloromethane (50mL×3) was added for extraction, washed with saturated brine (50mL×2), dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure, and the resulting residue was washed with 200-300 Separation on a silica gel column to obtain a yellow solid (2.48g, 87%).

[0041] 1 H NMR (600MHz, Chloroform-d) δ10.19(s,1H),7.51(s,1H),7.13(t,J=7.6Hz,1H),7.09(dd,J=7.6,1.5Hz,1H) ,6.93(t,J=7.3Hz,1H...

Embodiment 3

[0042] The synthesis of embodiment 3 intermediate 3

[0043]

[0044] Aluminum trichloride (1.98 g, 10 mmol) was added to anhydrous dichloromethane (15 mL), and then a solution of Intermediate 3 (1.42 g, 5 mmol) in anhydrous dichloromethane (5 mL) was added dropwise thereto. After the dropwise addition, the reaction was continued at 20° C. for 12 hours, and then hydrochloric acid solution (2M, 6 mL) was added to quench the reaction. Ethyl acetate (20mL×3) was added for extraction, washed with saturated brine (30mL×2), dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure, and the resulting residue was separated with a 200-300 mesh silica gel column to obtain a yellow solid ( 1.26g, 92.6%).

[0045]1 H NMR (600MHz, Chloroform-d) δ11.39 (s, 1H), 9.60 (d, J = 0.6Hz, 1H), 7.21–7.11 (m, 2H), 7.10 (dd, J = 7.7, 1.7Hz, 1H), 6.97(td, J=7.5, 1.3Hz, 1H), 6.92(dd, J=8.3, 1.3Hz, 1H), 6.39(s, 1H), 3.95(q, J=7.2Hz, 2H), 1.45(t,J=7.1Hz,3H).

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Abstract

The invention discloses a phenothiazine compound and a preparation method and application thereof. The phenothiazine compound is connected with a phenanthro[9,10-d]imidazole at a 3-position, the chemical structural formula of the phenothiazine compound is shown as a formula I, wherein R represents C1-C20 alkyls. By adding sodium hydroxide into a 2-methoxyl phenothiazine and halogenated alkane solution to prepare an intermediate 1 and introducing an aldehyde group, an intermediate 2 is obtained, the intermediate 2 is added into an anhydrous dichloromethane solution of anhydrous aluminum trichloride to obtain an intermediate 3, the intermediate 3 and phenanthrenequinone are dissolved in glacial acetic acid, and anhydrous ammonium acetate is added to obtain a target product through reaction.The compound can be used as a fluorescent probe to identify phosgene. The compound is stable in structure, simple and easy to obtain as a fluorescent probe and high in preparation yield, and has a certain application value.

Description

technical field [0001] The invention belongs to the technical field of synthesis of functional compounds, and relates to a phenothiazine compound and its preparation method and application, specifically a phenothiazine compound with phenanthrene[9,10-d]imidazole at the 3-position and its preparation method and uses. Background technique [0002] Phosgene, also known as carbonyl chloride, has two active acid chloride functional groups in its structure, which can react with nucleophilic groups such as hydroxyl and amino groups. Phosgene is colorless and highly toxic. Human beings exposed to phosgene at a concentration of 20ppm can cause respiratory and lung damage after 20 minutes. Prolonged time can even lead to death. Therefore, phosgene is used as a chemical weapon in wars and terrorist activities . Phosgene was responsible for 80% of the gas fatalities in World War I. The production and use of phosgene are strictly controlled and supervised in various countries. Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04C09K11/06G01N21/64
CPCC07D417/04C09K11/06C09K2211/1037C09K2211/1044G01N21/643G01N2021/6443
Inventor 汪珊后际挺
Owner XINYANG NORMAL UNIVERSITY
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