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Method for preparing prodiamine

A technology of amphetamine and dinitrobenzotrifluoride, which is applied in the field of compound preparation, can solve the problems affecting the content of amphetamine in the product and is not suitable for large-scale industrial production, so as to be suitable for large-scale industrial production, Short reaction time and good selectivity

Active Publication Date: 2010-06-09
MAX RUDONG CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because ammonia gas is very active, it is easy to generate by-products such as diammonia, which seriously affects the content of the product amproflurane
The two-step amination reactions reported in the literature are not suitable for large-scale industrial production

Method used

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  • Method for preparing prodiamine
  • Method for preparing prodiamine
  • Method for preparing prodiamine

Examples

Experimental program
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Effect test

Embodiment 1

[0017] 1) Add 2,4-dichloro-3,5-dinitrobenzotrifluoride and water into the reactor, stir, heat up to 40°C, add di-n-propylamine and potassium carbonate aqueous solution dropwise, and finish dropping in 25 minutes , after the dropwise reaction at 80°C for 1 hour, stop stirring and cooling to obtain N,N-di-n-propylamine-3-chloro-2,6-dinitro-4-trifluoromethylaniline, 2,4-dichloro The molar ratio of -3,5-dinitrobenzotrifluoride to di-n-propylamine is 1:1, and the molar ratio of potassium carbonate to 2,4-dichloro-3,5-dinitrobenzotrifluoride is 1:1 ;

[0018] 2) Add N,N-dimethylformamide and N,N-di-n-propylamine-3-chloro-2,6-dinitro-4-trifluorotoluidine in a weight ratio of 1:1, stir and pass Add ammonia gas to carry out diamination reaction for 1 hour. The diamination reaction temperature is 70° C., cool to 20° C., filter, wash the filter cake twice with water, and dry to obtain the product Amproflurane with a yield of 85.3%. The infrared spectrum of aminoproflurazine is shown in...

Embodiment 2

[0020] 1) Add 2,4-dichloro-3,5-dinitrobenzotrifluoride and water into the reactor, stir, heat up to 80°C, add di-n-propylamine and aqueous sodium bicarbonate solution dropwise, drop for 45 minutes After dropping, keep it warm at 90°C for 2 hours, stop stirring and cooling to get N,N-di-n-propylamine-3-chloro-2,6-dinitro-4-trifluoromethylaniline, 2,4-di The molar ratio of chloro-3,5-dinitrobenzotrifluoride to di-n-propylamine is 1:2, and the molar ratio of sodium bicarbonate to 2,4-dichloro-3,5-dinitrobenzotrifluoride is 1.8 : 1;

[0021] 2) Add acetonitrile and N,N-di-n-propylamine-3-chloro-2,6-dinitro-4-trifluorotoluidine in a weight ratio of 10:1, stir, and pass through ammonia gas for diamination reaction After 2 hours, the diamination reaction temperature was 140° C., cooled to 40° C., filtered, and the filter cake was washed with water for 3 times and dried to obtain the product Amproflurane with a yield of 85%.

Embodiment 3

[0023] 1) Add 2,4-dichloro-3,5-dinitrobenzotrifluoride and water into the reactor, stir, heat up to 50°C, and at the same time add di-n-propylamine and potassium hydroxide aqueous solution dropwise for 25 minutes After dropping, keep it warm at 80°C for 1 hour, stop stirring and cooling to get N,N-di-n-propylamine-3-chloro-2,6-dinitro-4-trifluoromethylaniline, 2,4-di The molar ratio of chloro-3,5-dinitrobenzotrifluoride to di-n-propylamine is 1:1, and the molar ratio of potassium hydroxide to 2,4-dichloro-3,5-dinitrobenzotrifluoride is 1 : 1;

[0024] 2) Add N-methylpyrrolidone and N,N-di-n-propylamine-3-chloro-2,6-dinitro-4-trifluorotoluidine in a weight ratio of 0.5:1, stir, and inject ammonia gas to carry out The diamination reaction was carried out for 1 hour. The diamination reaction temperature was 80° C., cooled to 20° C., filtered, the filter cake was washed 3 times with water, and dried to obtain the product Amprofluran with a yield of 85.4%.

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Abstract

The invention discloses a method for preparing prodiamine, which comprises the following steps: 1) adding 2,4-dichloro-3,5-dinitro trifluorotoluene and water in a reactor, heating and stirring the solution, dripping di-n-propylamine and inorganic base at the same time, and after the dripping is finished, keeping the temperature at 80 to 90 DEG C to perform an reaction for 1 to 2 hours and cooling the reaction solution to obtain N,N-di-n-propyl-amino-3-chloro-2,6- dinitro-4-trifluorotoluene; 2) adding a solvent and the N,N-di-n-propyl-amino-3-chloro-2,6- dinitro-4-trifluorotoluene in a ratio of 0.5:1 to 10:1, introducing ammonia to perform a reaction at a temperature of between 70 and 140 DEG C for 1 to 2 hour to form an diamine, cooling the reaction solution, filtering the reaction solution, and washing and drying the resulting product to obtain the prodiamine product. In the method, the reaction conditions are mild; the reaction time is short; the reaction selectivity is high; the generated prodiamine can precipitate from the solvent directly; the high purity product can be obtained after washing; and the reaction solvent can be recycled. The method has the advantages of simple process and equipment, simple operation and suitability for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of compounds, in particular to a preparation method of amphetamine. Background technique [0002] Amfluralin (also known as amfluralin) is a dinitroaniline herbicide. The compound has excellent contact and pre-emergence herbicide performance, and is widely used in grain and non-cultivated land to eliminate annual and perennial grass weeds. According to literature reports [US 3764623, US 3966816], the product is mainly prepared from 2,4-dichlorobenzotrifluoride through two-step nitration and two-step amination reactions. [0003] The monoamination reaction reported in the literature is to take 2,4-dichloro-3,5-dinitrobenzotrifluoride (dinitration product) and di-n-propylamine as raw materials, ethanol as a reaction solvent, and di-n-propylamine itself as an acid-binding agent, carried out under pressure, the reaction time is as long as 98 hours. Since the two chlorine atoms on the benzene ring hav...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/10
Inventor 郭群震蔡国平吴建文张位德
Owner MAX RUDONG CHEM
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