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Method for synthesizing compound of asymmetric substituted carbamide class from carbonylation

A chemical synthesis and asymmetric technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of urea derivatives, etc., can solve the problems of high price, achieve stable product quality, facilitate large-scale industrial production, and select reactions sex high effect

Inactive Publication Date: 2004-10-06
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the catalysts used in the reaction are expensive noble metals

Method used

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  • Method for synthesizing compound of asymmetric substituted carbamide class from carbonylation
  • Method for synthesizing compound of asymmetric substituted carbamide class from carbonylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 70mL stainless steel autoclave, add p-chloronitrobenzene (10mmol), Se (0.5mmol), 33% dimethylamine aqueous solution (20mmol), Et 3 N (1ml) and acetone (10ml), replaced by CO three times, raised the pressure of CO to 3MPa, put it into an oil bath that had risen to 135°C, stirred and reacted for 4h, cooled to room temperature, opened the kettle, and filtered the obtained The solid and the mother liquor were concentrated and the solid obtained by filtration was combined, recrystallized, dried, and weighed to obtain 1.0812g product N, N-dimethyl-N'-p-chlorophenylurea, and the HPLC analysis purity was more than 99.6%. It is 54.5% (in p-chloronitrobenzene) for the first single-pass yield, and the determination of content adopts Waters high-performance liquid chromatography system, including two 515 pumps, 486 type UV detectors, Spherisorb ODS-2 post (5 μ m, 4.6 × 250mm), with methanol-water as mobile phase, flow rate: 1mL / min, detector wavelength is λmax of each compound...

Embodiment 2

[0025] The organic solvent is benzene, and the experimental method and steps are the same as in Example 1. The HPLC analysis purity is more than 99%, and the actual first single-pass yield is 32.4% (in p-chloronitrobenzene).

Embodiment 3

[0027] The organic solvent is n-hexane, and the experimental method and steps are the same as in Example 1. The HPLC analysis purity is more than 99%, and the actual first-time single-pass yield is 35.6% (in terms of p-chloronitrobenzene).

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Abstract

A process for synthesizing the asymmetrically substituted urea compounds features that the arylnitro compound and organic amine take part in selective redox and carbonylation reaction at 50-200 deg.C under the existance of CO and the catalysis of Se as catalyst and triethylamine as cocatalyst. Its advantages are cyclic use of catalyst, high output rate, and high selectivity.

Description

technical field [0001] The invention relates to a method for synthesizing an asymmetric substituted urea compound, in particular to a method for synthesizing an asymmetric substituted urea compound through carbonylation. Background technique [0002] Asymmetric urea compounds containing substituted peptide bonds (-CONH-) have certain biological activities and can be used as pesticide products such as herbicides, insecticides and fungicides, as well as intermediates of fine chemical products such as medicines, pesticides and dyes. At present, the phosgene method or phosgene-like method is mainly used to synthesize these compounds in industry. Since phosgene is highly toxic and produces a large amount of corrosive chlorine-containing by-products during the reaction process, the equipment is severely corroded and is an environmental pollutant. In recent decades, people have been looking to explore alternatives to phosgene. A kind of noble metals such as Rh, Ru and Pd as the ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C273/18
Inventor 梅建庭陆世维原晓华杨瑛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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