Synthesis process of benzoyl substituted carbamide compound

A compound and substituted urea technology, which is applied in the field of catalytic carbonylation to synthesize benzoyl-substituted urea compounds, can solve the problems of large chlorine-containing by-products, harsh reaction conditions, highly toxic phosgene, etc., and achieves low reaction corrosion and raw materials. Simple, avoids the effect of the use of toxic phosgene

Inactive Publication Date: 2003-07-30
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the phosgene method or phosgene-like method is mainly used to synthesize these compounds in industry. The disadvantage is that phosgene is highly toxic and produces a large amount of corrosive chlorine-containing by-products during the reaction process, which are not only environmental pollutants, but also make Equipment is heavily corroded
In recent decades, people have been looking for ways to replace phosgene, (Document 1: Goodall B L.EP0398404, 1990; Document 2: Drent E, Prillwitz P E.EP 225673, 1987), a kind of noble metals such as Pd As a catalyst, CO is a carbonylation reagent, and the method of synthesizing benzoyl-substituted urea compounds from benzamide and aromatic nitro compounds has attracted more and more attention because of its few reaction steps, atom economy and environmental friendliness. Its shortcoming is that the catalyst used in the reaction is precious metals such as expensive palladium, and the reaction conditions are relatively harsh.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a 70mL stainless steel autoclave, add benzamide (20mmol), Se (0.5mmol), nitrobenzene (10mmol), Et 3 N (1ml) and toluene (10ml), replaced with CO three times, raised the pressure of CO to 3MPa, put it into an oil bath that had risen to 155°C, stirred and reacted for 10 hours, cooled to room temperature, opened the kettle, and filtered The resulting solid and the mother liquor were concentrated and then filtered to combine the resulting solid, recrystallized, dried, and weighed to obtain 1.7512g of the product 1-phenyl-3-benzoylurea. The HPLC analysis purity was more than 99.7%, and the actual yield was 65.1% (calculated as nitrobenzene). The content determination adopts Waters high-performance liquid chromatography system, including two 515 pumps, 486 type UV detector, Spherisorb ODS-2 column (5μm, 4.6×250mm), using methanol-water as mobile phase, flow rate: 1mL / min, detection The wavelength of the detector is λmax of each compound, column temperature: room temperatu...

Embodiment 2

[0018] The organic solvent is benzene, and the consumption is 10ml. Other experimental methods and conditions are the same as in Example 1. The HPLC analysis purity is more than 99%, and the actual yield is 63.2% (in terms of nitrobenzene).

Embodiment 3

[0020] The organic solvent was tetrahydrofuran, and the consumption was 10 ml. Other experimental methods and conditions were the same as in Example 1. The HPLC analysis purity was more than 99%, and the actual yield was 52.1% (in terms of nitrobenzene).

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Abstract

The synthesis process of benzoyl substituted carbamide compound is the reaction of benzamide and aryl nitro compound in organic solvent inside a sealed high pressure reactor in the presence of CO, Seas catalyst and triethylamine as cocatalyst. Where, the substitutent group of the phenyl group on the aryl nitro compound may be one or several electron donating group and / or electron withdrawing group; the molar ratio between benzamide and aryl nitro compound is 0.1-10; molar amount of Se is 0.1-20% of the minor reactant; molar amount of triethylamine is 10-200% of the minor reactant; the molar ratio between reactant and organic solvent is 0.021-1; the reactio period is 2-20 hr; the reaction temperature is 50-200 deg.C; and the CO pressure is 1-10 MPa gage pressure.

Description

technical field [0001] The invention relates to benzoyl-substituted urea compounds, in particular to a method for catalyzing carbonylation to synthesize benzoyl-substituted urea compounds. Background technique [0002] Benzoylurea compounds containing substituted peptide bonds (-CONHCONH-) have certain biological activities and can be used as pesticide products such as bioinsecticides and fungicides, and are also 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. The disadvantage is that phosgene is highly toxic and produces a large amount of corrosive chlorine-containing by-products during the reaction process, which are not only environmental pollutants, but also make The equipment is severely corroded. In recent decades, people have been looking for ways to replace phosgene, (Document 1: Goodall B L.EP0398404, 1990; Document 2: Dr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/54
Inventor 梅建庭陈金涛原晓华陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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