Preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide

A technology of phenylacetamide and phenylthioaniline, which is applied in the field of preparation of 2-methoxy-N-phenylacetamide, can solve the problems affecting the conversion rate of reduced product quality, reduction catalyst poisoning, wastewater treatment difficulties, etc. , to achieve the effects of green and environmentally friendly industrialized production, lower wastewater treatment costs, and easy industrialized production

Active Publication Date: 2020-11-24
CHANGZHOU YABANG QH PHARMACHEM +2
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, this process uses phosphorus trichloride as the chlorination agent, which will produce metaphosphoric acid as a by-product, which is a viscous substance that is easily wrapped by acylate, which will cause the reduction catalyst to be poisoned during the next reduction reaction and affect the conversion of the reaction. rate and quality of the reduced
At the same time, due to the generation of metaphosphoric acid, phosphorus is contained in wastewater, and wastewater treatment is difficult and expensive

Method used

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  • Preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide
  • Preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide
  • Preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide

Examples

Experimental program
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Effect test

Embodiment 1

[0029] In a 500ml four-necked flask, add 190g xylene and 75.0g condensate (0.3mol), 27.02g (0.3mol) methoxyacetic acid and 7.32g (0.06mol) 4-dimethylaminopyridine, start stirring, and heat up to 65 °C, 41.04 g (0.345 mol) of thionyl chloride was added dropwise, and the addition was completed in about 2 hours. After the dropwise addition, the temperature was raised to reflux at 140° C., and the temperature was kept at reflux for 5 hours. The temperature was lowered to 35° C., and 38 g of water was added dropwise for 0.5 hours. After static separation, the lower aqueous layer was separated, the upper organic layer was concentrated under reduced pressure, and 152 g of xylene was collected. Add 240 g of methanol, lower the temperature to 15° C., and stir for 0.5 hours. Filter with suction, wash with 30 g of methanol, and dry the filter cake at 70° C. for 10 hours. 91.8 g of light yellow solid 2-methoxy-N-(2-nitro-5-phenylthio)phenylacetamide was obtained, with a yield of 94.6%....

Embodiment 2

[0036] Add 450g cyclohexane and 75.0g condensate (0.3mol), 32.43g (0.36mol) methoxyacetic acid and 18.21g (0.18mol) triethylamine into a 1000ml four-necked flask, start stirring, and heat up to 70°C. 44.61 g (0.375 mol) of thionyl chloride was added dropwise, and the addition was completed in about 4 hours. After the dropwise addition, the temperature was raised to reflux at 80° C., and the temperature was kept at reflux for 8 hours. The temperature was lowered to 50° C., and 50 g of water was added dropwise for 1 hour. After static separation, the lower aqueous layer was separated, the upper organic layer was concentrated under reduced pressure, and 385 g of cyclohexane was collected. Add 220 g of ethanol, lower the temperature to 20° C., and stir for 1 hour. Filter with suction, wash with 30 g of ethanol, and dry the filter cake at 80° C. for 10 hours. 90.9 g of light yellow solid 2-methoxy-N-(2-nitro-5-phenylthio)phenylacetamide was obtained. Yield 93.8%. Melting point...

Embodiment 3

[0038] Add 350g toluene and 75.0g condensate (0.3mol), 32.43g (0.36mol) methoxyacetic acid and 14.24g (0.18mol) pyridine into a 1000ml four-neck flask, start stirring, raise the temperature to 75°C, and add 47.59g dropwise (0.4mol) thionyl chloride, and the addition was completed in about 4 hours. After the dropwise addition, the temperature was raised to reflux at 110° C., and the temperature was kept at reflux for 6.5 hours. The temperature was lowered to 80° C., and 90 g of water was added dropwise for 1 hour. After static separation, the lower aqueous layer was separated, the upper organic layer was concentrated under reduced pressure, and 315 g of toluene was collected. Add 320 g of methyl ethyl ketone, lower the temperature to 20° C., and stir for 1 hour. Filter with suction, wash with 30 g butanone, and dry the filter cake at 80° C. for 10 hours. 91.9 g of light yellow solid 2-methoxy-N-(2-nitro-5-phenylthio)phenylacetamide was obtained. Yield 94.8%. Melting point:...

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Abstract

The invention discloses a preparation method for 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide. The preparation method comprises the following steps: in a non-polar organic solvent, under catalysis of an acid binding agent, 2-nitro-5-phenylthio-aniline and methoxyacetic acid are added, and have a chlorination reaction with thionyl chloride under reflux; after the reaction ends, excess thionylchloride is decomposed by water, standing is performed for layering; the solvent is concentrated, a solvent with poor dissolvability is added for cooling crystallization, and suction filtration and drying are performed to obtain the 2-methoxy-N-(2-nitro-5-phenylthio) phenylacetamide. The preparation method adopts a one-pot method, and uses the thionyl chloride to replace phosphorus trichloride, so that the product purity reaches 99.8% or more, and the yield reaches 93.5% or more. The method has the advantages of being simple to operate, environmental-friendly, easy to industrially produce andthe like.

Description

technical field [0001] The invention relates to the technical fields of medicine and chemical industry, in particular to a preparation method of 2-methoxy-N-(2-nitro-5-phenylthio)phenylacetamide. Background technique [0002] The broad-spectrum anthelmintic drug Febante1, also known as benzoguanidine, is mainly used for the treatment and control of gastrointestinal roundworms, lungworms, tapeworms, etc. in cattle, sheep, pigs, horses and other animals. It has high efficiency and low toxicity , The residence time in the body is short, and the safety range is large. The chemical name of non-bantyr (1) is [[2-[(methoxyacetyl)amino]-4-(phenylthio)phenyl]carbimino]biscarbamate dimethyl ester, the first It was successfully developed by Bayer Pharmaceutical Company of Germany, and its synthetic route is rarely reported in China. [0003] [0004] During the preparation of Febantyr, one of the key intermediates is 2-methoxy-N-(2-nitro-5-phenylthio)phenylacetamide (2), which is ...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/41
CPCC07C319/20C07C323/41
Inventor 朱建民苏文杰王学成郁昕
Owner CHANGZHOU YABANG QH PHARMACHEM
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