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A method for catalytically synthesizing n,n'-disubstituted urea derivatives and imidazole derivatives

A technology for disubstituted urea and compound, which is applied in the field of synthesizing N,N'-disubstituted urea derivatives and imidazole derivatives, can solve the problems of complicated post-processing, few effective reuse times of catalysts, low catalytic activity and the like

Active Publication Date: 2017-10-03
TAIZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these solid-supported catalysts have more or less the following defects: compared with homogeneous catalysts, the catalytic activity is low, resulting in unsatisfactory reaction rate and yield; the number of effective catalyst reuse is less and the post-treatment is more complicated, etc.

Method used

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  • A method for catalytically synthesizing n,n'-disubstituted urea derivatives and imidazole derivatives
  • A method for catalytically synthesizing n,n'-disubstituted urea derivatives and imidazole derivatives
  • A method for catalytically synthesizing n,n'-disubstituted urea derivatives and imidazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add aniline (6mmol), dimethyl carbonate (3mmol) and catalyst (0.1g, 0.0275mmol) into a 50mL three-necked flask in turn, react at 80°C, react for 8 hours, TLC detects that the reaction of the raw materials is complete, add absolute ethanol ( 10 mL), refluxed and stirred for half an hour, cooled and crystallized, and the precipitated solid was vacuum dried to obtain the product with a yield of 70% and a content of 99%.

[0030] 1,3-Diphenylurea

[0031] 1 H NMR (400MHz, DMSO) (ppm): δ6.96 (t, 2H, J = 7.2Hz), 7.28 (t, 4H, J = 7.2Hz), 7.44 (d, 4H, J = 7.6Hz), 8.64 (s,2H); 13 C NMR (100MHz, DMSO): δ123.42, 127.02, 133.99, 144.93, 157.75. MS m / z: 212.09, Anal. Calcd for C 13 h 12 N 2 O: C, 73.56; H, 5.70; N, 13.20; O, 7.54; found C, 73.50; H, 5.74; N, 13.18; O, 7.58.

Embodiment 2

[0033] Add aniline (6mmol), dimethyl carbonate (3mmol) and catalyst (0.218g, 0.006mmol) into a 50mL three-necked flask in sequence, react at 100°C, react for 10 hours, TLC detects that the raw materials have not reacted completely, add absolute ethanol (10mL), refluxed and stirred for half an hour, cooled and crystallized, and the precipitated solid was vacuum-dried to obtain the product with a yield of 61% and a content of 98%.

Embodiment 3

[0035] Add aniline (6mmol), dimethyl carbonate (3.6mmol) and catalyst (0.1g, 0.0275mmol) into a 50mL three-neck flask in sequence, react at 80°C for 8 hours, and detect by TLC that the reaction of the raw materials is complete, then add absolute ethanol (10mL), refluxed and stirred for half an hour, cooled and crystallized, and the precipitated solid was vacuum dried to obtain the product with a yield of 69% and a content of 98%.

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Abstract

The invention relates to a green and efficient method for preparing N,N'-disubstituted urea derivatives and imidazole derivatives. The method for preparing N,N′-disubstituted urea derivatives through the condensation of aromatic amines and carbonates includes: using magnetic nanoparticle-supported ionic liquids as catalysts, under 60-100°C and normal pressure, under solvent-free conditions, aromatic amines and Carbonate condensation reaction for 8 to 14 hours to obtain the corresponding N,N′-disubstituted urea derivatives; using ionic liquid supported by magnetic nanoparticles as a catalyst, using ethanol as a solvent at 10 to 50°C and normal pressure to replace imidazole Addition reaction with electron-deficient olefin Michael for 1 to 5 hours to obtain the corresponding imidazole derivatives. Wherein, the catalyst is: it has been verified that after the reaction is completed, the catalyst can be simply recovered by applying an external magnetic field, and can be reused many times without obvious decrease in activity. The catalytic system is simple to operate, high in yield, good in reusability, and has good industrialization prospects.

Description

technical field [0001] The invention relates to an efficient, green method for synthesizing N,N'-disubstituted urea derivatives and imidazole derivatives by using a loaded functional ionic liquid as a catalyst. technical background [0002] In recent years, supported heterogeneous catalysis technology has attracted enough attention and has been widely used in organic synthesis as a green reaction technology (S.E.Davis, et al., Green Chem., 2013, 15, 17-45) . Carriers used for immobilization include mesoporous molecular sieves (MCM-41 and SBA-15), carbon and polymers, etc. (J.C.Bauer, et al., ACSCatal., 2012,2,2537-2546; Rev., 2008, 37, 2644-2657). However, these solid-supported catalysts have more or less the following defects: compared with homogeneous catalysts, the catalytic activity is low, resulting in unsatisfactory reaction rate and yield; the number of effective reuse of the catalyst is less and the post-treatment is more complicated. [0003] In order to avoid th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C273/18C07C275/28C07C275/34C07D233/92C07D233/56C07D235/06B01J31/28
CPCY02P20/584
Inventor 应安国陈钢杨健国侯海亮胡华南
Owner TAIZHOU UNIV