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Method for the synthesizing ormetoprim

A synthetic method, the technology of sodium methoxide, applied in the direction of organic chemistry, etc., can solve the problems of unfavorable labor protection and environmental protection, unfavorable for large-scale production, not easy to obtain, etc., and achieve the synthesis process of environmental protection, low cost and short synthesis cycle Effect

Inactive Publication Date: 2015-03-25
SUZHOU BUYUE PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Method 1: The raw materials are easy to obtain and the process is relatively simple, but the highly toxic acrylonitrile is used, which is very unfavorable for labor protection and environmental protection in large-scale production
Method two raw material 2-(methoxymethyl)-3-methoxypropionitrile is very expensive and not easy to obtain, high economic cost and unfavorable for large-scale production

Method used

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  • Method for the synthesizing ormetoprim
  • Method for the synthesizing ormetoprim
  • Method for the synthesizing ormetoprim

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1, the synthesis of Omeprene

[0019] Sodium methoxide (270g, 5mol) was slowly added to methanol (900mL) solution, then 3-methoxypropionitrile (170g, 2mol) and 4,5-dimethoxy-2-methylbenzene were added to the reaction solution Formaldehyde (180g, 1mol), and react at 50-55°C for 24 hours, then add guanidine hydrochloride (191g, 2mol) in batches, and react at 50-55°C for 24 hours, cool to room temperature, filter, and wash the filter cake with a small amount of water , Obtain Omepleline (197g) after product drying, yield 72%. White solid, melting point: 232.5~233.0℃, 1 HNMR (500MHz, d 6 -DMSO):8.2(br s,2H),7.8(br s,2H),6.86(s,1H),6.83(s,1H),6.75(s,1H),3.76(s,3H),3.73( s,3H), 3.58(s,2H), 2.15(s,3H).

Embodiment 2

[0020] Embodiment 2, the synthesis of Omeprene

[0021] Sodium methoxide (216g, 4mol) was slowly added to methanol (900mL) solution, and then 3-methoxypropionitrile (127.5g, 1.5mol) and 4,5-dimethoxy-2-methane were added to the reaction solution Base benzaldehyde (180g, 1mol), and reacted at 55~60°C for 18 hours, then added guanidine hydrochloride (143g, 1.5mol) in batches, and reacted at 55~60°C for 18 hours, cooled to room temperature, filtered, filter cake After washing with a small amount of water, the product was dried to obtain Omepleline (200g), with a yield of 73%. White solid, melting point: 232.5~233.0℃, 1 HNMR (500MHz, d 6 -DMSO):8.2(br s,2H),7.8(br s,2H),6.86(s,1H),6.83(s,1H),6.75(s,1H),3.76(s,3H),3.73( s,3H), 3.58(s,2H), 2.15(s,3H).

Embodiment 3

[0022] Embodiment 3, the synthesis of Omeprene

[0023] Sodium methoxide (162g, 3mol) was slowly added to methanol (900mL) solution, then 3-methoxypropionitrile (85g, 1mol) and 4,5-dimethoxy-2-methylbenzene were added to the reaction solution Formaldehyde (180g, 1mol), and react at 60-64°C for 18 hours, then add guanidine hydrochloride (95g, 1mol) in batches, and react at 60-64°C for 18 hours, cool to room temperature, filter, and wash the filter cake with a small amount of water , Obtain Omepleline (178g) after product drying, yield 65%. White solid, melting point: 32.5~233.0℃, 1 HNMR (500MHz, d 6 -DMSO):8.2(br s,2H),7.8(br s,2H),6.86(s,1H),6.83(s,1H),6.75(s,1H),3.76(s,3H),3.73( s,3H), 3.58(s,2H), 2.15(s,3H).

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Abstract

The invention belongs to the field of veterinary drugs, particularly relates to a method for the synthesizing ormetoprim. The method comprises the following steps of: (A), adding 3-methoxypropionitrile in a sodium methoxide solution for a condensation reaction by taking 4,5-dimethoxy-2-methyl-benzaldehyde as a raw material; (B), adding guanidine hydrochloride into the reaction mixture obtained in the step (A), and preform a cyclization reaction to obtain the ormetoprim. According to the one-pot method for synthesizing the ormetoprim, the low-cost 3-methoxypropionitrile replaces the virulent acrylonitrile, so that the synthesis process is environment-friendly, less in reaction step, and short in synthesis period; and the raw material is readily available, low in cost and simple in operation, and the method has broad prospects for large-scale industrial application.

Description

Technical field: [0001] The invention belongs to the field of veterinary drugs, and more specifically relates to a synthetic method of omeprene. Background technique: [0002] Omeprene is a commonly used antibacterial synergist in animal husbandry and aquaculture. Due to the complexity of its molecular structure, the synthesis method is generally more complicated. U.S. Patents US2007049609, US20050209260, US4143227 and journals Journal of Organic Chemistry; vol.57; nb.13; (1992); p.3531-3535 etc. have reported the preparation method of omeprene, and its synthetic route is respectively as follows figure 1 and figure 2 shown. Method one: react with 4,5-dimethoxyl-2-methylbenzaldehyde and acrylonitrile, and then cyclize with guanidine carbonate to obtain Omeprene ( figure 1 ). Method two: take 2-(methoxymethenyl)-3-methoxypropionitrile as raw material to ring-close with guanidine hydrochloride, and then react with 3,4-dimethoxytoluene to synthesize omeprene ( figure 2 )....

Claims

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Application Information

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IPC IPC(8): C07D239/49
CPCC07D239/49
Inventor 周盛峰冯志勇陈龙宋斌虞心红
Owner SUZHOU BUYUE PHARMA CO LTD
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