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N-(6-hydroxyl hexyl) carbazole derivatives and synthesis method of N-(6-hydroxyl hexyl) carbazole and its derivative

A technology of carbazole derivatives and synthetic methods, applied in the direction of organic chemistry, can solve the problems of lower final product yield, increased synthesis cost, long reaction time, etc., and achieve convenient separation and purification, good tolerance and universality, The effect of high reaction efficiency

Inactive Publication Date: 2019-02-22
LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method is cumbersome and requires a long reaction time. At the same time, the three-step synthesis greatly reduces the yield of the final product and leads to an increase in synthesis cost.

Method used

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  • N-(6-hydroxyl hexyl) carbazole derivatives and synthesis method of N-(6-hydroxyl hexyl) carbazole and its derivative
  • N-(6-hydroxyl hexyl) carbazole derivatives and synthesis method of N-(6-hydroxyl hexyl) carbazole and its derivative
  • N-(6-hydroxyl hexyl) carbazole derivatives and synthesis method of N-(6-hydroxyl hexyl) carbazole and its derivative

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Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1, a kind of synthetic method of N-(6-hydroxyhexyl) carbazole is carried out according to the following steps: add carbazole 1.67g (10mmol) successively in single-necked flask, benzyltriethylammonium chloride 150mg, two Methyl sulfoxide 20ml, saturated sodium hydroxide 15ml, 6-bromo-n-hexanol 1.57ml (12mmol), react at 65°C for 4h under magnetic stirring. Add 100ml of deionized water and 100ml of ethyl acetate, separate the liquids, wash the organic phase with water several times until the solution is neutral (generally 3 times), separate the organic phase and add anhydrous sodium sulfate to dry, filter, and remove ethyl acetate by rotary evaporation under reduced pressure Esters, and the residue was separated by silica gel column chromatography (eluent: dichloromethane) to obtain 2.54 g of white solid N-(6-hydroxyhexyl)carbazole with a yield of 95%. Synthetic route such as figure 2 shown.

[0028] Product N-(6-hydroxyhexyl) carbazole characterization data ...

Embodiment 2

[0034] Embodiment 2, a kind of synthetic method of N-(6-hydroxyhexyl) carbazole is carried out as follows: add carbazole 1.67g (10mmol) successively in single-necked flask, tetrabutylammonium bromide 75mg, N, N - Dimethylformamide 15ml, saturated potassium hydroxide 10ml, 6-bromo-n-hexanol 10.02mmol, react at 45°C for 3.5h under magnetic stirring. Add 100ml of deionized water and 100ml of ethyl acetate, separate the liquids, wash the organic phase with water several times until the solution is neutral (generally 3 times), separate the organic phase and add anhydrous sodium sulfate to dry, filter, and remove ethyl acetate by rotary evaporation under reduced pressure Esters, and the residue was separated by silica gel column chromatography (eluent: dichloromethane) to obtain 2.14 g of white solid N-(6-hydroxyhexyl)carbazole with a yield of 50%.

Embodiment 3

[0035] Embodiment 3, a kind of synthetic method of N-(6-hydroxyhexyl) methoxycarbazole, carries out according to the following steps:

[0036] Add 1.97g (10mmol) of methoxycarbazole, 150mg of benzyltriethylammonium chloride, 20ml of dimethyl sulfoxide, 15ml of saturated sodium hydroxide, and 1.57ml (12mmol) of 6-bromo-n-hexanol in a single-necked flask. , Reacted at 65°C for 4h under magnetic stirring. Add 100ml of deionized water and 100ml of ethyl acetate, separate the liquids, wash the organic phase with water several times until the solution is neutral (generally 3 times), separate the organic phase and add anhydrous sodium sulfate to dry, filter, and remove ethyl acetate by rotary evaporation under reduced pressure Esters, and the residue was separated by silica gel column chromatography (eluent: dichloromethane) to obtain 2.7 g of white solid N-(6-hydroxyhexyl)methoxycarbazole with a yield of 90%. Synthetic route such as Figure 4 shown.

[0037] Product N-(6-hydroxyh...

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Abstract

The invention discloses an N-(6-hydroxyl hexyl) carbazole derivatives and a synthesis method of N-(6-hydroxyl hexyl) carbazole and its derivative. Carbazole or its derivatives and a transfer catalystare dissolved in an organic solvent and then a saturated alkaline solution and 6-bromohexanol are added to make the carbazole or its derivatives fully react with the 6-bromohexanol, separation is performed to obtain the N-(6-hydroxyl hexyl) carbazole and its derivative. The N-(6-hydroxyl hexyl) carbazole and its derivative is synthesized through the synthesis method in a one-step way and have highreaction efficiency, low reaction cost and high substrate suitability and are very suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to the technical field of synthesis of nitrogen-containing aromatic heterocyclic compounds, in particular to a synthetic method of N-(6-hydroxyhexyl)carbazole derivatives and N-(6-hydroxyhexyl)carbazole and derivatives thereof. Background technique [0002] N-(6-hydroxyhexyl)carbazole and its derivatives are an important class of nitrogen-containing aromatic heterocyclic compounds, which contain a large conjugated system and strong intramolecular electron transfer in the molecule. The ring structure makes carbazoles have excellent chemical stability and electron flow properties. The electron-rich structure makes it easy for N-(6-hydroxyhexyl)carbazole and its derivatives to undergo a nucleophilic substitution reaction on the carbazole ring, and conveniently introduce various functional groups to adjust the photoelectric properties of the molecule. More importantly, due to the presence of hydroxyl sites, N-(6-hydroxyhexyl)carbazol...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88
CPCC07D209/86C07D209/88
Inventor 钟全洁张林罗炫
Owner LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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