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Synthesis method of N, N-dimethyl-2-chloro nicotinamide

A technology of chloronicotinamide and synthesis method, applied in directions such as organic chemistry, can solve the problems of slow reaction speed, hydrolysis, reduction of N,N-dimethyl-2-chloronicotinamide production rate and yield, etc. The utilization rate of nicotine chlorine and the effect of reducing the hydrolysis of nicotine chlorine

Inactive Publication Date: 2012-01-25
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Nicosulfuron is a sulfonylurea herbicide used in the post-emergence 3-5 leaf stage of corn and the 2-4 leaf stage of annual weeds. The currently reported process route is to obtain nicotinic acid N -Oxide, and then hydrogenated and ammonolysis one-pot reaction to get N, N-dimethyl-2-chloronicotinamide, that is, directly use dimethylamine aqueous solution and 2-chloronicotinyl chloride in the two systems, at a lower N, N-dimethyl-2-chloronicotinic acid amide was prepared at the reaction temperature, but during the reaction, the aqueous phase and the organic phase were isolated from each other, and the reactants could not be contacted, resulting in an extremely slow reaction rate, and at the same time, it was easy to cause organic bottom The hydrolysis of the product reduces the production rate and yield of N, N-dimethyl-2-chloronicotinamide

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 75.1g 33% (0.55mol) dimethylamine aqueous solution to a 500ml three-necked flask equipped with stirring, thermometer and tail gas absorbing device, add 0.5g tetrabutylammonium bromide, add dropwise 45.0g N, N-dimethylamine at room temperature Base-2-chloronicotinoyl chloride and 150.0g dichloroethane solution, the temperature of the cold water bath is controlled to not exceed 25°C, the dropwise addition is completed in about 1.5 hours, and the reaction is continued at 25°C for 1 hour. Stop stirring, let it stand for half an hour, separate layers, extract the water layer twice with 50g×2 dichloroethane, combine the organic layers, recover dichloroethane by atmospheric distillation to 110°C, and continue to recover dichloromethane by distillation under reduced pressure Ethane to 110°C / 0.096mPa, stop heating, drop to about 70°C, stop vacuum, pour out the material while it is hot, weigh it, and take a sample for analysis. Content 99%, yield 99%.

Embodiment 2

[0017] Add 75.1g33% (0.55mol) dimethylamine aqueous solution in a 500ml three-necked flask equipped with stirring, thermometer and tail gas absorption device, add 3.2g benzyltriethylammonium chloride, add dropwise 45.0g N, N- Dimethyl-2-chloronicotinoyl chloride and 150.0g of dichloroethane solution, the temperature of the cold water bath is controlled to not exceed 20°C, the dropwise addition is completed in about 1.5 hours, and the reaction is continued at 20°C for 0.4 hours. Stop stirring, let it stand for half an hour, separate layers, extract the water layer twice with 50g×2 dichloroethane, combine the organic layers, recover dichloroethane by atmospheric distillation to 110°C, and continue to recover dichloromethane by distillation under reduced pressure Ethane to 110°C / 0.096mPa, stop heating, drop to about 70°C, stop vacuum, pour out the material while it is hot, weigh it, and take a sample for analysis. Content 99%, yield 99%.

Embodiment 3

[0019] Add 75.1g 33% (0.55mol) aqueous solution of dimethylamine to a 500ml three-necked flask equipped with stirring, thermometer and tail gas absorbing device, add 9g benzyltrimethylammonium chloride, add dropwise 45.0g N, N-dimethylammonium chloride at room temperature Methyl-2-chloronicotinoyl chloride and 150.0g of dichloroethane solution, the cold water bath controls the dropping temperature not to exceed 22°C, the dropwise addition is completed in about 1.5 hours, and the reaction is continued at 22°C for 1.2 hours. Stop stirring, let stand for half an hour, separate layers, extract the water layer twice with 50g×2 dichloroethane, combine the organic layers, recover dichloroethane by atmospheric distillation to 110°C, change to vacuum distillation to continue recovery of dichloroethane Ethane to 110°C / 0.096mPa, stop heating, drop to about 70°C, stop vacuum, pour out the material while it is hot, weigh it, and take a sample for analysis. Content 99%, yield 99%.

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Abstract

The invention relates to a synthesis method of an intermediate of agricultural herbicide nicosulfuron, which comprises rapid reaction of dichloroethane solution and dimethylamine agueous solution of acyl chloride under conditions with a phase transfer catalyst. The problem of fumigachlorin hydrolysis is solved, and the dimethylamine agueous solution can be successfully applied in production of the intermediate of N, N-dimethyl-2-chloro nicotinamide.

Description

technical field [0001] The invention relates to a synthesis method of an intermediate of the agricultural herbicide nicosulfuron. Background technique [0002] Nicosulfuron is a sulfonylurea herbicide used in the 3-5 leaf stage of corn and the 2-4 leaf stage of annual weeds. The currently reported process route is to use nicotinic acid and oxidize it with hydrogen peroxide to obtain nicotinic acid N -Oxide, and then hydrogenated and ammonolysis one-pot reaction to get N, N-dimethyl-2-chloronicotinamide, that is, directly use dimethylamine aqueous solution and 2-chloronicotinyl chloride in the two systems, at a lower N, N-dimethyl-2-chloronicotinamide was prepared at the reaction temperature. However, during the reaction, the aqueous phase and the organic phase were isolated from each other, and the reactants could not be contacted, resulting in a very slow reaction rate and easy to cause organic bottoms. The hydrolysis of the product reduces the production rate and yield of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82
Inventor 于国权吕良忠王建荣吉志扬
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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