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Synthesis method for dibenzoxazole compounds

A synthesis method and benzoxazole technology are applied in the synthesis field of bisbenzoxazole compounds, can solve the problems of long reaction time, unfavorable environment, large amount of alkali, etc., and achieve short reaction time, less three wastes and low cost Effect

Active Publication Date: 2008-03-19
SHENYANG RES INST OF CHEM IND +1
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0005] In order to overcome the disadvantages of long reaction time, large consumption of acid and alkali, and unfavorable environment when preparing bisbenzoxazole compounds in the prior art, the present invention proposes a new synthetic method of bisbenzoxazole compounds : Direct ring-closing condensation of aromatic dinitrile compound and substituted or unsubstituted o-aminophenol hydrochloride to prepare target product

Method used

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  • Synthesis method for dibenzoxazole compounds
  • Synthesis method for dibenzoxazole compounds
  • Synthesis method for dibenzoxazole compounds

Examples

Experimental program
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Effect test

example 1

[0035] 11.5 g (0.05 mol) of 4,4'-dicyanostyrene, 16 g (0.11 mol) of o-aminophenol hydrochloride, and 90 g of nitrobenzene were respectively put into a 150 ml three-necked bottle. Sealed, vacuumed, replaced with nitrogen. Raise the temperature to 190-200°C, stir rapidly and keep warm for 3 hours, and the reaction is completed. Cool down, filter and dry. 19.5 g of 4,4'-bis(benzoxazol-2-yl)stilbene was obtained.

example 2

[0037] 9 g (0.05 mol) of naphthalene-1,4-dinitrile, 16 g (0.11 mol) of o-aminophenol hydrochloride, and 90 g of sulfolane were respectively put into a 150 ml three-necked flask. Sealed, vacuumed, replaced with nitrogen. Raise the temperature to 200-230° C., stir rapidly and keep warm for 3 hours, and the reaction is completed. 17 g of 1,4-bis(benzoxazol-2-yl)naphthalene was obtained.

example 3

[0039] In a 150ml three-necked bottle, 11.5g (0.05mol) of 4,4'-dicyano-stilbene, 8g (0.055mol) of o-aminophenol hydrochloride, and 8.8g (0.055mol) of o-amino-p-cresol hydrochloride ), sulfolane 80g. Sealed, vacuumed, replaced with nitrogen. Raise the temperature to 190-200°C, stir rapidly and keep warm for 3 hours, and the reaction is completed. Cool down, filter and dry. 19 g of a bisbenzoxazole stilbene mixture was obtained.

[0040] Determine the percentage composition of the mixture with liquid chromatography as:

[0041] 4-(Benzoxazol-2-yl)-4'-(5-methylbenzoxazol-2-yl)stilbene 49%; 4,4'-bis(benzoxazol-2- base) stilbene 24%; 4,4'-bis(5-methylbenzoxazol-2-yl) stilbene 27%.

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Abstract

The invention discloses a synthesis method of a dibenzoxazole type compound. In organic sovlent, a closed-loop condensation reaction is directly carried out between an aromatic dinitrile compound and substituted or nonsubstituted o-aminophenol hydrochloride to synthesize the dibenzoxazole compound or compounds with different substituents, and the composite proportion of the compound can be regulated according to different raw material proportionings. The method has the advantages of smooth reaction process, short reaction time, high yield rate of products, low cost, little three wastes, environmental protection, etc. and better faciliates large-scale production. The product produced by the method can be applied to the fluorescent whiting of synthesized or natural polymeric materials.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing bisbenzoxazole compounds. Background technique [0002] Usually, the method of synthesizing bisbenzoxazole compounds is to use dicarboxylic acid or its acyl chloride as raw material to condense with o-aminophenol compounds at high temperature to form symmetrical compounds, or to form them through secondary condensation with o-aminophenols of different substituents. asymmetric compound. This preparation method has the disadvantages of harsh reaction conditions, low yield and low product purity. [0003] When using nitrile group-containing compounds and o-aminophenols to prepare benzoxazole compounds, it is usually necessary to undergo an imidate reaction process. Although the reaction conditions are mild, the reaction time is long, and a large amount of acid, alkali and other chemical substances are consumed, which is unfavorable to the environment. Th...

Claims

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Application Information

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IPC IPC(8): C07D263/57C07D413/14C07D263/00C07D333/00
Inventor 李文胜竹百均王景国徐会志刘月中钱之杨
Owner SHENYANG RES INST OF CHEM IND
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