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A kind of synthetic method of n-cyclopropyl-[[(2-methoxybenzoyl) amino]sulfonyl]benzamide

A technology of methoxybenzoyl and carboxybenzenesulfonamide, which is applied in the field of synthesis of N-cyclopropyl-[[amino]sulfonyl]benzamide, and can solve the problems of low purity, long reaction time, corrosion of equipment, etc. problems, to achieve the effect of high product yield, quality advantages, and reduced emissions

Active Publication Date: 2018-02-06
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN100413848 reports its synthetic method, but using chloroform as the reaction solvent has poor selectivity, low purity, relatively large amount of chlorination reagent, complex process, long reaction time, and acid gas sulfur dioxide and hydrogen chloride, which corrode equipment and pollute the air. , is not conducive to the promotion and application of
The reaction temperature is high, the cost is high, it is not environmentally friendly and economical

Method used

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  • A kind of synthetic method of n-cyclopropyl-[[(2-methoxybenzoyl) amino]sulfonyl]benzamide
  • A kind of synthetic method of n-cyclopropyl-[[(2-methoxybenzoyl) amino]sulfonyl]benzamide
  • A kind of synthetic method of n-cyclopropyl-[[(2-methoxybenzoyl) amino]sulfonyl]benzamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 203.22g p-carboxybenzenesulfonamide (1mol), 167.33g o-methoxybenzoic acid (1.1mol), 1.1g p-toluenesulfonic acid in a four-neck flask, stir in 600g toluene solvent for 0.5 hours, heat up and reflux for 4 hours to clear;

[0025] Cool down to 40°C, add 180g of thionyl chloride dropwise into the bottle, and keep warm for 3 hours after the dropwise addition. The solvent was removed, and 650 g of dichloromethane was added for infiltration to obtain a dichloromethane solution of 4-[[(2-methoxybenzoyl)amino]sulfonyl]benzoyl chloride.

[0026] Add dichloromethane (70g) and 74.8g cyclopropylamine (1.3mol) to another four-neck flask, control the temperature at -8°C, and under stirring, 4-[[(2-methoxybenzoyl)amino]sulfonyl A dichloromethane solution of acyl]benzoyl chloride and 200 g of aqueous sodium hydroxide (30% by mass fraction) were added dropwise to the system. After the dropwise addition, the mixture was kept at -4°C for 9 hours, and filtered by suction at -2°C to ob...

Embodiment 2

[0028] Add 101.1g p-carboxybenzenesulfonamide (0.5mol content 99% 200.19), 86g o-methoxybenzoic acid (0.56mol 152.12), 1g benzenesulfonic acid in 250g toluene solvent and stir for 1 hour in a four-necked flask, then heat up and reflux React for 6 hours until clear;

[0029] Cool down to 45°C, add 78.1g of thionyl chloride (1.3eq 118.98) dropwise into the bottle, and keep warm for 4 hours after the dropwise addition is completed. The solvent was removed, and 300 g of dichloromethane was added for infiltration to obtain a dichloromethane solution of 4-[[(2-methoxybenzoyl)amino]sulfonyl]benzoyl chloride.

[0030] Add dichloromethane (40g) and 30.2g cyclopropylamine (1.05eq) to another four-neck flask, control the temperature at -5°C, and stir the 4-[[(2-methoxybenzoyl)amino]sulfonate A dichloromethane solution of acyl]benzoyl chloride and 120 g of aqueous sodium hydroxide (30% by mass fraction) were added dropwise to the system. After the dropwise addition was completed, the mi...

Embodiment 3

[0032] Add 2235g p-carboxybenzenesulfonamide (11mol, content 99%), 1506g o-methoxybenzoic acid (content 99%, 10mol), 335g p-nitrobenzenesulfonic acid in 4500g toluene solvent and stir for 1 hour in the four-necked flask , heating and reflux reaction for 3 hours until clear;

[0033] Cool down to 50°C, add 1562g of thionyl chloride dropwise into the bottle, and keep warm for 5 hours after the dropwise addition. The solvent was removed, and 3000 g of dichloromethane was added for infiltration to obtain a dichloromethane solution of 4-[[(2-methoxybenzoyl)amino]sulfonyl]benzoyl chloride.

[0034] Add dichloromethane (4000g) and 806g cyclopropylamine to another four-neck flask, control the temperature at -6°C, and under stirring, 4-[[(2-methoxybenzoyl)amino]sulfonyl]benzoyl chloride The dichloromethane solution and 1860g aqueous sodium hydroxide solution (mass fraction 30%) were added dropwise to the system. After the dropwise addition was completed, the mixture was kept at -5°C ...

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Abstract

The invention relates to a synthesis method of N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide. The method comprises that 4-carboxybenzenesulfonamide as a raw material undergoes a reaction in the presence of an acid as a catalyst to produce N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide. A high efficiency catalyst reduces a chlorination reagent use amount by 40%, discharge of acidic gas such as sulfur dioxide and hydrogen chloride is greatly reduced, technical requirements of energy saving, consumption reduction and environmental protection are satisfied, a product yield is high, product purity is high, and the synthesis method has advantages in cost and quality and has a large development space in industrial production.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a synthesis method of N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide. Background technique [0002] N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide, English name Cyprosulfamide, molecular formula: C 18 h 18 N 2 o 5 S, molecular weight 374.41, structural formula as follows: [0003] [0004] N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide is an acylsulfamoylbenzamide compound discovered by Bayer in 1997. As a herbicide safener, since 2008, it has grown at a double-digit growth rate every year, making it effective in controlling more than 65 kinds of grass weeds and broad-leaved weeds, such as wild millet, crabgrass, Amaranth, foxtail, goosegrass, quinoa, barnyardgrass and Abutilon, etc. [0005] U.S. Patent (WO9916744) describes acylsulfamoylbenzamide derivatives and their use as safeners for controlling weeds in herbicides. The safe herb...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/40C07C303/36C07C311/51
CPCC07C303/36C07C303/40C07C311/51
Inventor 王帅帅逄廷超张华曹学兵曹同波王杰秀
Owner JINGBO AGROCHEM TECH CO LTD
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