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Preparation process of 6'-nitroindolyline benzspriothiane

A technology for benzospirothiopyran and nitroindoline, which is applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve the problems of difficult industrial operation, high cost, harsh conditions for synthesizing spirothiopyran, and the like, Achieve the effect of low preparation cost and simple operation

Inactive Publication Date: 2006-11-15
WUHAN UNIV
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Problems solved by technology

[0004] The method for synthesizing spirothiopyran reported in the previous literature has relatively harsh conditions and high cost, and is not easy to carry out actual industrial operation. After continuous research and improvement, the present invention proposes a simple and easy-to-operate method to provide a basis for mass production

Method used

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  • Preparation process of 6'-nitroindolyline benzspriothiane
  • Preparation process of 6'-nitroindolyline benzspriothiane
  • Preparation process of 6'-nitroindolyline benzspriothiane

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preparation example Construction

[0023] 2.1 Preparation of 5-nitrosalicylaldehyde

[0024] First prepare an ice-salt bath (ice:salt is about 3:1), and the temperature is about -20°C. Take o-chlorobenzaldehyde in a 250ml three-neck flask, cool it in an ice-salt bath, and slowly add concentrated sulfuric acid dropwise therein under vigorous stirring, and the reaction solution turns light yellow at this time. Continue to add mixed acid (10ml fuming nitric acid+14ml concentrated sulfuric acid) to it, and the reaction solution slowly turns dark red. Keep the temperature for 3h. Slowly pour the reaction solution into a beaker filled with ice cubes while stirring, a large amount of yellow precipitates are formed. Suction filtration and drying gave a light yellow solid. After recrystallization from absolute ethanol, 5-nitrosalicylaldehyde was obtained which was close to white.

[0025] 2.2 Preparation of 25-nitrothiosalicylaldehyde

[0026] Weigh Na 2 S·9H 2 O was added to a 100ml three-necked flask, and disti...

Embodiment

[0033] Add 9.2ml of 3-methyl-2-butanone to 9.2g of freshly distilled phenylhydrazine, and the reaction is exothermic. The oil bath was heated to reflux at 80°C for 4 hours. After the reaction, separate the layers, discard the water layer, and wash the oil layer with anhydrous MgSO 4 After drying, 13.5 g of crude hydrazone was obtained. Add 30ml of glacial acetic acid to the hydrazone obtained above, react in a 90°C water bath for 3 hours, raise the temperature to 150°C, and evaporate most of the solvent, about 16ml. Cool to room temperature, wash with saturated NaCO 3 The solution neutralizes the reaction solution. The aqueous and organic phases are separated. The aqueous phase was extracted with diethyl ether, and the extract was combined with the organic phase and washed with anhydrous MgSO 4 dry. Distill at normal pressure to collect the solvent, then distill under reduced pressure to collect the fraction at 85-90°C / 0.25Kpa to obtain 6.9g of light yellow oily liquid, ...

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Abstract

A process for preparing 6-nitroindoline benzospiropyranium includes such steps as dissolving 5-nitrothio salicyladehyde and 1,2,3,3-tetramethyl indoline iodide in absolute alcohol, adding hexahydropyridine as catalyst, reflux reaction, concentrating, filtering and drying.

Description

technical field [0001] The present invention relates to the preparation method of 6'-nitroindoline benzospirothiopyran. Background technique [0002] After Hirshberg proposed the scientific significance of photochromism for the first time, the research on photochromism broke away from the previous aimlessness and randomness. The specific performance of photochromic materials has brought broad and important application prospects to photochromic compounds, such as optical information recording materials, molecular wires, molecular switches, etc. [0003] The most important characteristics of organic photochromic materials with practical application prospects are that the color forming bodies must have sufficient thermal stability, and the second is the fatigue resistance of photochromic compounds. At present, most of the research on photochromism is concentrated on diarylethene, fulgid anhydride, spiropyran, spirooxazine, azos and related heterocyclic compounds, and at the sa...

Claims

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Application Information

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IPC IPC(8): C07D495/10C09K9/02
Inventor 张旭吴峰颜肖慈罗明道邓南圣
Owner WUHAN UNIV
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