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Preparation method of 3-n-butylamino-N-phenylmaleimide compound

A technology based on maleimide and n-butylamine, which is applied in the field of preparation of 3-n-butylamino-N-phenylmaleimide compounds, can solve the problem of high price, long reaction route and side effects. There are many products, etc., to achieve the effects of easy industrial production, simple reaction operation, and shortened reaction time

Inactive Publication Date: 2016-09-21
DONGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Above-mentioned three kinds of synthesis methods all have the shortcoming such as too long reaction route, many by-products, low yield, meanwhile, the raw material used in the third method is difficult to obtain, expensive, increases production cost
Therefore, these three methods are not suitable for large-scale synthesis

Method used

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  • Preparation method of 3-n-butylamino-N-phenylmaleimide compound
  • Preparation method of 3-n-butylamino-N-phenylmaleimide compound
  • Preparation method of 3-n-butylamino-N-phenylmaleimide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Take 17.3g (0.1mol) of N-phenylmaleimide, 7.31g (0.1mol) of n-butylamine, and 13.7g (0.05mol) of silver carbonate and add them to a 250mL round bottom flask, then add 100mL of chlorobenzene, and heat Stir at 120°C for 4 hours, after the reaction is complete, add 50 mL of water, stir for 5 minutes, extract with 200 mL of ethyl acetate x 3, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and recrystallize the obtained solid with 95% ethanol to obtain a yellow-brown solid 3 -n-butylamino-N-phenylmaleimide 17.59g, yield 72%, mp: 128-130°C.

Embodiment 2

[0043] Take 17.3g (0.1mol) of N-phenylmaleimide, 14.63g (0.2mol) of n-butylamine, and 27.5g (0.10mol) of silver carbonate and add them to a 250mL round bottom flask, then add 100mL of chlorobenzene, and heat Stir at 100°C for 4 hours, after the reaction is complete, add 50 mL of water, stir for 5 minutes, extract with 200 mL of ethyl acetate x 3, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and recrystallize the obtained solid with 95% ethanol to obtain a yellow-brown solid 3 -n-butylamino-N-phenylmaleimide 19.54g, yield 80%, mp: 128-130°C.

Embodiment 3

[0045] Take 8.65g (0.05mol) of N-phenylmaleimide, 7.31g (0.1mol) of n-butylamine, and 13.7g (0.05mol) of silver carbonate and add them to a 250mL round bottom flask, then add 100mL of chlorobenzene, and heat Stir at 120°C for 8 hours. After the reaction is complete, add 50 mL of water, stir for 5 minutes, extract with 300 mL of ethyl acetate x 3, dry the organic phase with anhydrous sodium sulfate, evaporate the solvent, and recrystallize the obtained solid with 95% ethanol to obtain a yellow-brown solid 3 -n-butylamino-N-phenylmaleimide 10.38g, yield 85%, mp: 128-130°C.

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Abstract

The invention relates to a preparation method of a 3-n-butylamino-N-phenylmaleimide compound. The 3-n-butylamino-N-phenylmaleimide compound has the structural formula shown in the description. The preparation method comprises the following steps: adding N-phenylmaleimide, n-butylamine and a catalyst into a reaction solvent, heating to 25-120 DEG C, enabling reaction for 1-24 hours and purifying to obtain the 3-n-butylamino-N-phenylmaleimide compound. The 3-n-butylamino-N-phenylmaleimide compound prepared by the preparation method provided by the invention is simple in reaction operation, relatively high in yield, short in reaction route, less in generation of waste gas, waste liquid and waste solid and easy to achieve industrial production.

Description

technical field [0001] The invention belongs to the field of 3-amino-N-substituted maleimide compounds and the preparation thereof, in particular to a preparation method of 3-n-butylamino-N-phenylmaleimide compounds. Background technique [0002] 3-N-butylamino-N-phenylmaleimide compound (I) and its derivatives are important drug synthesis intermediates, and have a wide range of biological activities such as antibacterial and antitumor, as well as the synthesis and application of fluorescent materials. Preparation (Mori, K.; Izawa, T.; Matsui, S. Antifouling N-arylmaleimide derivatives. JP 53032119,1978; Augustin, M.; Koehler, M.; Kazandji, S.. Sulfurization of C-substituted maleimide, Tetrahedron ,1984,40(18),3499-502.; Mabrie,A.B.; Robin,M.P.; Quan,W.D.; Willcock,H.; dependent emission, Chemical Communications, 2015, 51(47):9733-9736.). [0003] The synthetic method of the maleimide compound of 3-amino-N-substitution of bibliography mainly comprises three kinds: [0004...

Claims

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Application Information

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IPC IPC(8): C07D207/456
CPCC07D207/456
Inventor 赵圣印安玉龙
Owner DONGHUA UNIV
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