Preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide

A technology of dimethylnicotinamide and aminosulfonyl, which is applied in the field of preparation of 2-aminosulfonyl-N,N-dimethylnicotinamide, can solve problems such as poor process stability, low cost, blackened sulfur, etc. problems, to avoid the use of polysulfides, to achieve good yield and quality, and to achieve mild reaction conditions.

Active Publication Date: 2017-01-04
ANHUI RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] As shown in the above equation, 2-chloronicotinic acid is usually used as a raw material, and the product is obtained through four stages of "amidation, vulcanization, oxychlorination and amination", with low cost and high reaction yield, but the second stage " Vulcanization", replacing 2-chlorine atoms with polysulfides, the amount of sulfur is even as high as 3eqv. Excessive elemental sulfur is ox

Method used

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  • Preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide
  • Preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide

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Embodiment 1

[0061] 1) Synthesis of intermediate II (2-amino-N,N-dimethylnicotinamide):

[0062] 17.46g (100mmol) of 2-aminonicotinic acid hydrochloride and 100mL of chlorobenzene were mixed in a 250mL round bottom flask, stirred at room temperature, and 14.86g (125mmol) of thionyl chloride was added dropwise. After the dropwise addition, the system was heated to Stir at 50-55°C for 1 h, and distill under reduced pressure to remove excess thionyl chloride and half chlorobenzene, and maintain the system volume at about 60 mL. Heat and stir to raise the temperature of the system to 80°C, slowly pass in about 5.4g (120mmol) of dimethylamine gas, and keep stirring at this temperature for 30 minutes after passing through, then cool down to 0°C, a large amount of solids are precipitated, and suction filtered to obtain 2 -Amino-N,N-dimethylnicotinamide 15.44g, yield 93.6%, content 96.7%, m.p.83-85°C.

[0063] 2) Synthesis of diazonium salt III (2-diazonium chloride-N,N-dimethylnicotinamide):

...

Embodiment 2

[0070] 1) Synthesis of intermediate (2-amino-N,N-dimethylnicotinamide):

[0071] 17.46g (100mmol) of 2-aminonicotinic acid hydrochloride and 100mL of chlorobenzene were mixed in a 250mL round bottom flask, stirred at room temperature, and 14.86g (125mmol) of thionyl chloride was added dropwise. After the dropwise addition, the system was heated to Stir at 50-55°C for 1 h, and distill under reduced pressure to remove excess thionyl chloride and half chlorobenzene, and maintain the system volume at about 60 mL. Heat and stir to raise the temperature of the system to 80°C, slowly pass in about 5.4g (120mmol) of dimethylamine gas, and keep stirring at this temperature for 30 minutes after passing through, then cool down to 0°C, a large amount of solids are precipitated, and suction filtered to obtain 2 -Amino-N,N-dimethylnicotinamide 15.44g, yield 93.6%, content 96.7%, m.p.83-85°C.

[0072] 2) Synthesis of diazonium salt III (2-diazonium chloride-N,N-dimethylnicotinamide):

[00...

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Abstract

The invention provides a preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide. With 2-aminonicotinic acid serving as the raw material, 2-aminosulfonyl-N,N-dimethylnicotinamide is prepared through the first step of conducting a chloroformylation reaction and an amination reaction, the second step of conducting a diazotization reaction, the third step of conducting a Sandmeyer reaction and the fourth step of conducting an amination reaction. The preparation method has the advantages that reaction conditions are mild, stable and controllable, side reactions are not likely to occur as the number of active sites is small, and the whole route is high in yield and quality; cost can be effectively reduced as original materials can be easily obtained from the market, and the preparation method is environmentally friendly as no polysulfide is used.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide. Background technique [0002] Nicosulfuron was developed by Ishihara Co., Ltd. of Japan. It is a sulfonylurea herbicide for corn fields, with high efficiency, low toxicity and safety. After the patent expired in 2007, the price dropped significantly, and it has become the main variety of domestic corn field herbicides. 2-Aminosulfonyl-N,N-dimethylnicotinamide is an important synthetic intermediate, and its synthetic methods mainly include the pyridine sulfinate amination method reported in EP0353944 and EP0547035; the sulfonyl chloride amino group reported in EP232067 and US4786734 Chemical method, the latter is the most common method used in domestic industrial production. [0003] [0004] As shown in the above equation, 2-chloronicotinic acid is usually used as a raw material, and the product is obtained thr...

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Application Information

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IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 胡仁涛阮班锋田国栋陈蔚林
Owner ANHUI RES INST OF CHEM IND
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