Synthesis process of N-substituted pyrrole

A synthesis method and pyrrole technology, applied in organic chemistry and other directions, can solve the problems of complex catalyst preparation method, inability to recycle and apply, serious environmental pollution, etc., and achieve the effects of mild reaction conditions, no three wastes, and less dosage.

Inactive Publication Date: 2007-03-21
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs double the amount of amine in excess, and the preparation method of the catalyst is complicated, cannot be recycled and applied mechanically, the yield is medium, and the environmental pollution is serious. Therefore, it is of great economic benefit to develop a green chemical synthesis method of N-substituted pyrrole with high efficiency and environmental protection and social benefits

Method used

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  • Synthesis process of N-substituted pyrrole
  • Synthesis process of N-substituted pyrrole
  • Synthesis process of N-substituted pyrrole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The ratio of the feed materials of diketone, amine and ytterbium trifluoromethanesulfonate is 1:1:0.05, the diketone is 2,5-hexanedione, and the amine is aniline.

[0025] In a 50ml four-neck flask equipped with a thermometer, a reflux condenser and a mechanical stirrer, add 11.4g (0.1mol) of 2,5-hexanedione, 9.3g (0.1mol) of aniline, and 3.1g of ytterbium trifluoromethanesulfonate ( 5 mmol), heated to 50°C, and reacted for 30 minutes. Simultaneously, HPLC was followed and monitored (flow rate: 1.5 ml / min, acetonitrile: water: acetic acid=40:60:0.1). After the reaction was completed, cool to room temperature, filter and wash the filter cake with water, and collect the precipitated white solid by filtration again to obtain 15.2 g of the product N-phenyl-2,5-dimethylpyrrole, with a yield of 89%, a purity of 99.6%, and a melting point of 50.2~51.1℃, the recovery rate of ytterbium trifluoromethanesulfonate is 91.2%.

Embodiment 2

[0027] The ratio of feed materials of diketone, amine and zinc trifluoromethanesulfonate is 1:1:0.05, the diketone is 2,5-hexanedione, and the amine is aniline. 11.4 g (0.1 mol) of 2,5-hexanedione, 9.3 g (0.1 mol) of aniline, and 1.8 g (5 mmol) of zinc trifluoromethanesulfonate.

[0028] Others are the same as in Example 1 to obtain 13.7 g of the product N-phenyl-2,5-dimethylpyrrole, with a yield of 86%, a purity of 99.2%, and a melting point of 50.2 to 51.4°C. The reactant is used as a solvent for zinc trifluoromethanesulfonate Or 92.2% recovery in organic solvents.

Embodiment 3

[0030] The ratio of the feed materials of diketone, amine and lanthanum trifluoromethanesulfonate is 1:1:0.05, the diketone is 2,5-hexanedione, and the amine is aniline. 11.4 g (0.1 mol) of 2,5-hexanedione, 9.3 g (0.1 mol) of aniline, and 2.9 g (5 mmol) of lanthanum trifluoromethanesulfonate.

[0031] Others were the same as in Example 1 to obtain 15.0 g of the product N-phenyl-2,5-dimethylpyrrole with a yield of 88%, a purity of 99.0%, a melting point of 50.1-51.0°C, and a recovery rate of lanthanum trifluoromethanesulfonate of 94.1%.

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Abstract

The present invention is green synthesis process of N-substituted pyrrole as shown in expression I. The N-substituted pyrrole is prepared with diketone as shown in expression II and amine as shown in expression III as materials, the trifluoro mesylate of RE element or transition element as catalyst, and the reactant as solvent or added organic solvent, and through reaction at 0-150 deg.c for 10 min to 24 hr, filtering the reacted liquid to obtain filter cake, dissolving the filter cake in water and further filtering out the insoluble matter as the N-substituted pyrrole compound. The present invention has high reaction yield over 85 %, reasonable technological path, mild reaction condition, reusable catalyst consumption and no wastes produced basically.

Description

(1) Technical field [0001] The invention relates to a green chemical synthesis method of N-substituted pyrrole. (2) Background technology [0002] Pyrrole compounds are widely used in the synthesis of pesticides and medicines, and have high practical value. In the prior art, the chemical synthesis of pyrrole compounds is prepared in an organic solvent using a traditional Lewis acid catalyst. As proposed in Tetrahedron Letters 2003, 44(20), 3923-3925, N-substituted pyrrole was prepared by using 1,4-diketone and 100% excess amine under the action of a metal composite catalyst. This method requires an excessive amount of double amine, and the catalyst preparation method is complicated, cannot be recycled and applied mechanically, the yield is medium, and the environmental pollution is serious. Therefore, it is of great economic benefit to develop an efficient and environmentally friendly green chemical synthesis method for N-substituted pyrroles and social benefits. (3) Con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/323C07D401/04C07D409/04C07D207/00C07D213/00C07D333/00
Inventor 苏为科陈久喜吴华悦
Owner WENZHOU UNIVERSITY
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