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Synthesis of n,n-dimethyl-n-phenyl-(n-fluorodichloromethylthio)-sulfonamide

A technology of fluorodichloromethylthio and fluorodichloromethylsulfanyl is applied in the field of synthesis technology of N,N-dimethyl-N-phenyl-sulfonamide, and can solve the problem of difficult industrial production of sulfonamide, The problems of high environmental hazard and high raw material cost have achieved the effect of simple post-processing, low environmental hazard, and reduced equipment condition requirements.

Active Publication Date: 2016-03-30
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The technical problem to be solved by the present invention is that the cost of raw materials in the existing method is high, the "three wastes" produced are very harmful to the environment, and the yield is very low and unstable, which leads to N,N-dimethyl-N-phenyl- (N-fluorodichloromethylthio)-sulfonamide is difficult to produce industrially

Method used

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  • Synthesis of n,n-dimethyl-n-phenyl-(n-fluorodichloromethylthio)-sulfonamide
  • Synthesis of n,n-dimethyl-n-phenyl-(n-fluorodichloromethylthio)-sulfonamide
  • Synthesis of n,n-dimethyl-n-phenyl-(n-fluorodichloromethylthio)-sulfonamide

Examples

Experimental program
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Effect test

Embodiment 1

[0053] Synthesis of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide:

[0054]

[0055] a. Add N,N-dimethyl-N'-phenylsulfonamide to toluene, add sodium hydride at 0-5°C, and react at room temperature for 0.5-1 hour;

[0056] b. Drop in a toluene solution with a mass concentration of 65-90% fluorodichloromethylsulfonyl chloride, and react at room temperature for 1-2 hours; N,N-dimethyl-N'-phenylsulfonamide and fluorodichloro The molar ratio of methylsulfonyl chloride is 1:0.8; the molar ratio of N,N-dimethyl-N'-phenylsulfonamide and sodium hydride is 1:1.0; N,N-dimethyl-N'-benzene The mass ratio of methyl sulfonamide and toluene is 1:6.0;

[0057] c. adding water to wash the reaction solution, and obtain an organic phase after liquid separation;

[0058] d. The organic phase is dried and concentrated to obtain the crude product of the product, and then refined to obtain the pure product of the product.

[0059] The mass ratio of crude N,N-dimethyl-N-phenyl-(...

Embodiment 2

[0062] The synthesis process of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide is similar to Example 1, the difference is: N,N-dimethyl-N'-benzene The molar ratio of sulfonamide and fluorodichloromethylsulfonyl chloride is 1:1.4; the molar ratio of N,N-dimethyl-N'-phenylsulfonamide and sodium hydride is 1:1.2; N,N-di The mass ratio of methyl-N'-phenylsulfonamide to toluene is 1:8.65. The yield of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide in this example was 84.2%. TLC: Pet:EA=5:1, Rf=0.5. 1 HNMR(CDCl3,300MHz)δ:2.76(s,6H,NCH3),7.36-7.44(m,3H),7.49-7.52(m,2H); 9 FNMR (CDCl3, 300MHz) δ: -27.30.

Embodiment 3

[0064] The synthesis process of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide is similar to Example 1, the difference is: N,N-dimethyl-N'-benzene The molar ratio of sulfonamide and fluorodichloromethylsulfonyl chloride is 1:2.0; the molar ratio of N,N-dimethyl-N'-phenylsulfonamide and sodium hydride is 1:1.5; N,N-di The mass ratio of methyl-N'-phenylsulfonamide and toluene is 1:10. The yield of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide in this example was 82.6%. TLC: Pet:EA=5:1, Rf=0.5. 1 HNMR (CDCl 3 ,300MHz)δ:2.78(s,6H,NCH 3 ),7.36-7.44(m,3H),7.49-7.52(m,2H); 9 FNMR (CDCl 3 ,300MHz) δ: -27.30.

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Abstract

The invention discloses a process for synthesizing N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide. The synthesis process comprises the following steps: by taking ferric fluoride as a fluoride, recrystallizing a toluene solution of fluorodichloromethylsulfuryl chloride and N,N-dimethyl-N'-phenyl sulfamide under a certain reaction conditions so as to prepare the N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide. According to the synthesis process, an intermediate is synthesized, the utilization rate and yield of the intermediate can be improved in the intermediate preparation process, the residual substances are conveniently recycled after the reaction, the cost is greatly saved, and the environmental pollution is reduced. The ferric fluoride is taken as the fluoride in the intermediate synthesis process, so that the yield of the N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide is improved, the influence on the environment is slight, and the problems that the N,N-dimethyl-N-phenyl-(N-fluorodichloromethylmercapto)-sulfamide is difficultly produced industrially because the raw material cost is high, the generated three industrial wastes have great damage to the environment and the yield is low and instable in the conventional method and the like are solved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to a synthesis process of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide. Background technique [0002] N,N-Dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide, commonly known as antibacterial, is a broad-spectrum protective fungicide with a wide bactericidal spectrum, which is effective against Escherichia coli, Staphylococcus aureus and Candida albicans have strong inhibitory effect. It can prevent botrytis and is also an acaricide. It is mainly used to prevent fungal diseases such as citrus, grapes and other fruits and vegetables. Because it has antibacterial detoxification and rapid antipruritic effects, it has also become an effective antibacterial ingredient in some cosmetics and external medicines. [0003] The structural formula of N,N-dimethyl-N-phenyl-(N-fluorodichloromethylthio)-sulfonamide: [0004] [0005] The synthesis of N,N-d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C307/10C07C303/34
Inventor 黄永学亢兴龙王银谢国斌何燕郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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