Synthesis of benzoxazolinone

A technology of benzoxazolinone and synthesis method, which is applied in the field of synthesis of benzoxazolinone compounds, can solve the problems of corroded equipment, complicated operation, highly toxic phosgene and the like, and achieves less three wastes and mild reaction conditions. , Easy to clean production effect

Inactive Publication Date: 2003-02-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantage is that phosgene is highly toxic, and a large amount of corrosive chlorine-containing by-products are produced during the reaction process, which not only severely corrodes equipment, but also easily pollutes the environment
This method is obviously cumbersome to operate
The total yield is not too high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add ortho-nitrophenol (10mmol), Se (0.5mmol), DBU (10mmol), triethylamine (20mmol) and toluene 10ml in the stainless steel autoclave of 70ml, raise CO pressure to 3MPa after CO replacement three times, It was put into an oil bath at 160°C and stirred for 3 hours, cooled to room temperature, the reaction solution was concentrated, and subjected to column chromatography. The eluent was petroleum ether: ethyl acetate (5:3), and the eluent was concentrated to obtain the product. The yield was 44.4%. Melting point (mp) 137-138°C.

Embodiment 2

[0019] Add ortho-nitrophenol (10mmol), Se (0.5mmol), DBU (10mmol), triethylamine (20mmol) and toluene 10ml in the stainless steel autoclave of 70ml, raise CO pressure to 3MPa after CO replacement three times, It was put into an oil bath at 160°C and stirred for 5 hours, cooled to room temperature, the reaction solution was concentrated, and subjected to column chromatography. The eluent was petroleum ether: ethyl acetate (5:3), and the eluent was concentrated to obtain the product. The yield was 51.8%. mp137-138°C.

Embodiment 3

[0021] Add ortho-nitrophenol (10mmol), Se (0.5mmol), DBU (10mmol), triethylamine (20mmol) and toluene 10ml in the stainless steel autoclave of 70ml, raise CO pressure to 3MPa after CO replacement three times, It was put into an oil bath at 160°C and stirred for 7 hours, then cooled to room temperature, the reaction solution was concentrated, and subjected to column chromatography. The eluent was petroleum ether: ethyl acetate (5:3), and the eluent was concentrated to obtain the product. The yield was 66.7%. mp137-138°C.

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Abstract

A synthesis process of benzoxazolinone is a reaction process is organic solvent in a sealed high pressure reactor with CO and o-nitrophhenol as raw material, Se as catalyst, DBU and triethylamine as cocatalyst. The molar amount of Se is 0.1-20 % that of reactant, organic strong alkali DBU 10-200 %, triethylamine 10-200%, the molar ratio of reactant to the solvent is 1 to 1-50, the reaction time is 2-20 hr, the reaction temperature is 50-200 deg.C and CO reactant pressure is 1-10 MPa gauge pressure. The present invention has simple operation, easy-to-obtain material, fewer reaction steps and high yield.

Description

technical field [0001] The invention relates to the synthesis of a benzoxazolone compound, in particular to a method for catalyzing carbonylation to synthesize a benzoxazoline compound. Background technique [0002] Benzoxazoline is an important fine chemical. It can be used as an anti-mold and anti-fungal agent for polymer materials, and an anti-mold agent for grains. At present, the conventional method for synthesizing benzoxazolinone mainly adopts the phosgene method or the phosgene-like method. Its disadvantage is that phosgene is highly toxic, and a large amount of corrosive chlorine-containing by-products are produced during the reaction process, which not only severely corrodes equipment, but also easily pollutes the environment. At the same time, the conventional synthesis of benzoxazolinone mainly adopts a two-step method, that is, aromatic nitro compounds are first reduced to aromatic amino compounds, and then reacted with phosgene or phosgene substitutes to prep...

Claims

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Application Information

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IPC IPC(8): C07D263/58
Inventor 凌冈陈金铸陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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