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A kind of preparation method of 2-chloro-n,n-dimethylnicotinamide

A technology of dimethyl nicotinamide and alkyl, which is applied in the field of preparation of 2-chloro-N,N-dimethyl nicotinamide, can solve the problems of large amount of waste water, high cost of raw materials, unfavorable industrial production and the like

Active Publication Date: 2021-06-08
江苏丰山生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, its raw material 2-chloro-3-trichloromethylpyridine is not easy to get, the raw material cost is high, and the pH control requirements of the reaction are relatively high, and the amount of waste water produced is relatively large, which is unfavorable for industrialized production

Method used

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  • A kind of preparation method of 2-chloro-n,n-dimethylnicotinamide
  • A kind of preparation method of 2-chloro-n,n-dimethylnicotinamide
  • A kind of preparation method of 2-chloro-n,n-dimethylnicotinamide

Examples

Experimental program
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Effect test

Embodiment 1

[0042] 1) Synthesis of 2-cyano-5-dimethylamino-N,N-dimethyl-2,4-pentadienamide

[0043]Add 19.8 g (0.2 mol) of 3-dimethylaminoacrolein, 2-cyano-N, N-dimethylethyl Amide (22.4g, 0.2mol) and toluene (180ml), stirred mechanically at room temperature, added acetic acid (2.4g, 0.04mol) and 40% dimethylamine aqueous solution (4.5g, 0.04mol) successively, stirred and heated to reflux at 120°C Water was separated, followed by liquid phase tracking until the reaction was complete, and the reaction was carried out for 11 hours. After the reaction was completed, solvent removal was performed to obtain 38.44 g of brown solid 2-cyano-5-dimethylamino-N,N-dimethyl-2,4-pentadienamide, with a content of 97.5% and a yield of 97.1%.

[0044] 2) Synthesis of 2-chloro-N,N-dimethylnicotinamide

[0045] Add 2-cyano-5-dimethylamino-N,N-dimethyl-2,4-pentadienamide (38.4g, 0.194mol) and dichloroethane (150ml) into a 350ml pressure bottle , stirred and dissolved at 5°C, fed dry hydrogen chloride gas ...

Embodiment 2

[0047] 1) Synthesis of 2-cyano-5-di-n-propylamino-N,N-dimethyl-2,4-pentadienamide

[0048] Add 31.0 g (0.2 mol) of 3-di-n-propylaminoacrolein, 2-cyano-N, N-dimethylethyl Amide (22.4g, 0.2mol) and toluene (180ml), stirred mechanically at room temperature, added acetic acid (2.4g, 0.04mol) and 40% dimethylamine aqueous solution (4.5g, 0.04mol) successively, stirred and heated to reflux at 120°C Water was separated, followed by liquid phase tracking until the reaction was complete, and the reaction was carried out for 14 hours. After the reaction was completed, solvent removal was performed to obtain 49.75 g of brown solid 2-cyano-5-di-n-propylamino-N,N-dimethyl-2,4-pentadienamide, with a content of 97.8% and a yield of 97.7%.

[0049] 2) Synthesis of 2-chloro-N,N-dimethylnicotinamide

[0050] Add 2-cyano-5-di-n-propylamino-N,N-dimethyl-2,4-pentadienamide (49.7g, 0.195mol) and dichloroethane (150ml) into a 350ml pressure bottle , stirred and dissolved at 10°C, fed dry hydrogen...

Embodiment 3

[0052] 1) Synthesis of 2-cyano-5-di-n-propylamino-N,N-dimethyl-2,4-pentadienamide

[0053] Add 31.0 g (0.2 mol) of 3-di-n-propylaminoacrolein, 2-cyano-N, N-dimethylethyl Amide (22.4g, 0.2mol) and toluene (180ml), stirred mechanically at room temperature, added acetic acid (3.6g, 0.06mol) and 40% dimethylamine aqueous solution (6.75g, 0.06mol) successively, stirred and heated to reflux at 120°C Divide the water, follow the liquid phase to detect the complete reaction, and react for 6 hours. After the reaction was completed, solvent removal was performed to obtain 49.85 g of brown solid 2-cyano-5-di-n-propylamino-N,N-dimethyl-2,4-pentadienamide, with a content of 97.5% and a yield of 97.6%.

[0054] 2) Synthesis of 2-chloro-N,N-dimethylnicotinamide

[0055] Add 2-cyano-5-di-n-propylamino-N,N-dimethyl-2,4-pentadienamide (49.8g, 0.195mol) and dichloroethane (150ml) into a 350ml pressure bottle , stirred and dissolved at 10°C, fed dry hydrogen chloride gas until the pressure was...

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Abstract

A preparation method of 2-chloro-N, N-dimethylnicotinamide, the method first disubstituted aminoacrolein and 2-cyano-N, N-dimethylacetamide under the conditions catalyzed by a catalyst Carrying out Knoevenagel reaction, the obtained target intermediate is reacted with hydrogen chloride gas to obtain 2-chloro-N,N-dimethylnicotinamide. The catalyst used in the present invention can greatly improve the yield of the Novenger reaction, the yield can reach more than 97%, and the content can reach more than 97%. The invention has easy-to-obtain raw materials, simple operation, improves the reaction yield, avoids the use of highly toxic reagents such as phosphorus oxychloride and thionyl chloride, has less discharge of three wastes, is environmentally friendly, saves production costs, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of preparation of herbicide intermediate compounds, in particular to a preparation method of 2-chloro-N,N-dimethylnicotinamide. Background technique [0002] Nicosulfuron is a sulfonamide herbicide discovered by Ishihara Industry Company of Japan and jointly developed with DuPont Company of the United States in 1987-1988. Nicosulfuron is a highly selective systemic herbicide, which mainly controls weeds by inhibiting acetolactase, absorbed by stems and leaves, and can control annual and perennial grass weeds and some broad-leaved weeds. [0003] Nicosulfuron is a cornfield herbicide. At present, the annual demand for Nicosulfuron in the international market is 5,000 tons. From 2011 to 2015, my country's corn planting area was about 20 million hectares, and the planting area has surpassed that of cereals to rank first. In 2013, the global annual sales of nicosulfuron was about 290 million US dollars, and nicosulfuron...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 孙旭峰瞿保华沈明王晋阳李俊卿单永祥
Owner 江苏丰山生化科技有限公司
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