Method for synthesizing symmetrical compound of aroma urea group

A compound, aromatic urea technology, which is applied in the field of synthesizing symmetrical aromatic urea compounds, can solve problems such as unfavorable industrialization, and achieve the effect of less equipment investment, simple and safe operation

Inactive Publication Date: 2005-06-15
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

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Problems solved by technology

[0003] Catalytic carbonylation of amines or nitro compounds into urea with complexes of transition metals (such as Pd, Rh, Ru) has been reported, but obtaining high yields requires more catalysts, which is unfavorable for industrialization [Ahmcd.M.T; Jens.W .Chem.Rev.1996.94.1047]

Method used

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  • Method for synthesizing symmetrical compound of aroma urea group
  • Method for synthesizing symmetrical compound of aroma urea group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add nitrobenzene 15mmol, Se 0.38mmol, H 2 O 1.0ml, KOH 5.0mmol and solvent DMF 10.0ml, continue to pass through carbon monoxide, heat to 88 ° C and stir for 12 hours, cool to room temperature, switch carbon monoxide to oxygen or air and stir for several hours, filter out selenium powder, in the obtained Water was added to the filtrate for recrystallization, and 1.52 g of diphenylurea was isolated with a yield of 95.7%. (according to nitrobenzene calculation), the product is identified through melting point determination and NMR.

Embodiment 2

[0022] The base is NaOH, and the time is 9 hours. Other experimental methods and conditions are the same as in Example 1, and the yield is 37.1% (calculated according to nitrobenzene).

Embodiment 3

[0024] base is CH 3 CO 2 K1.8mmol, the reaction time was 12 hours, other experimental methods and conditions were the same as in Example 1, and the productive rate was 95.0% (calculated according to nitrobenzene).

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Abstract

A process for synthesizing the symmetric arylurea compound features that the aromatic nitro compound takes part in carbonylation reaction in organic solvent under existance of CO, Se powder as catalyst and alkali as cocatalyst to obtani target produst. The Se powder is then oxidized by O2 or air for separating it out and reusing it.

Description

technical field [0001] The invention relates to a method for synthesizing symmetrical aromatic urea compounds, in particular to a method for synthesizing symmetrical aromatic urea compounds through selenium-catalyzed carbonylation of aromatic nitro compounds using carbon monoxide under normal pressure. Background technique [0002] Symmetrical aromatic ureas are a large class of important organic synthesis intermediates and raw materials. The previous synthesis methods used highly toxic phosgene and produced a large amount of chlorine-containing by-products during the reaction process, which caused serious corrosion to the equipment. Bigger trouble, so people began to look for non-phosgene methods. [0003] Catalytic carbonylation of amines or nitro compounds into urea with complexes of transition metals (such as Pd, Rh, Ru) has been reported, but obtaining high yields requires more catalysts, which is unfavorable for industrialization [Ahmcd.M.T; Jens.W .Chem.Rev.1996.94.1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C273/00C07C275/28
Inventor 王小芳陆世维余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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