Synthesis method of 1-((3-(5-nitro-2-furyl)allylidene)amino) hydantoin

A technology of nitrofuran acrolein and allylidene, which is applied in the direction of organic chemistry and the like, can solve the problems of aggravating environmental impact pressure, poor atom economy, increasing production cost, etc., and achieves improved atom economy, less three wastes, and reduced generation. Effect

Pending Publication Date: 2018-10-30
黄石法姆药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] The main disadvantage of this process is: the atom economy of the reaction is poor, and as the raw material nitrofurantoin itself is a kind of furan anti-infective drug, the cost is higher
The existing processes all have technical defects such as too long reaction route, low yield, and large pollution, which aggravates the pressure of environmental impact and increases production cost.

Method used

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  • Synthesis method of 1-((3-(5-nitro-2-furyl)allylidene)amino) hydantoin
  • Synthesis method of 1-((3-(5-nitro-2-furyl)allylidene)amino) hydantoin
  • Synthesis method of 1-((3-(5-nitro-2-furyl)allylidene)amino) hydantoin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] In a 3000L reactor, add 2400kg of 5% propylaminohydantoin solution, 150kg of 5-nitrofuran acrolein and 400kg of N,N-dimethylformamide (DMF) in sequence, and heat to 90~ React at 100°C for 1.5 hours, cool to room temperature, add 400kg of water to dilute and precipitate a brown-yellow solid, filter, wash with water, wash with ethanol and dry to obtain a brown-yellow powder, which is then dissolved in N,N-dimethylformamide, decolorized, and refined , washing with ethanol to obtain orange powder, drying to obtain target product 1-((3-(5-nitro-2-furyl) allyl) amino) hydantoin 180kg, yield 80%, also obtain propylene base amino solid.

Embodiment 2

[0045] In a 3000L reactor, add 2400kg of 5% propylaminohydantoin solution, 160kg of 5-nitrofuran acrolein and 400kg of N,N-dimethylformamide (DMF) in sequence, and heat to 90~ React for 1 hour at 100°C, cool to room temperature, add 400kg of water to dilute and precipitate a brownish-yellow solid, filter, wash with water, wash with ethanol and dry to obtain a brownish-yellow powder, which is then dissolved in N,N-dimethylformamide, decolorized, and refined , washing with ethanol to obtain orange-yellow powder, drying to obtain the target product 1-((3-(5-nitro-2-furyl) allylidene) amino) hydantoin 175kg, yield 79%, also obtain propylene base amino solid.

Embodiment 3

[0047]In a 3000L reactor, add 2400kg of 5% propylaminohydantoin solution, 160kg of 5-nitrofuran acrolein and 400kg of N,N-dimethylformamide (DMF) in sequence, and heat to 90~ React at 100°C for 2 hours, cool to room temperature, add 400kg of water to dilute and precipitate a brown-yellow solid, filter, wash with water, wash with ethanol and dry to obtain a brown-yellow powder, which is then dissolved in N,N-dimethylformamide, decolorized, and refined , washing with ethanol to obtain orange powder, drying to obtain the target product 1-((3-(5-nitro-2-furyl) allylidene) amino) hydantoin 185kg, yield 83%, HPLC analysis purity The ratio was 99.5%, and a solid of propyl amino was obtained.

[0048] The 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin compound prepared in Examples 1-3 was verified by ultraviolet, infrared, nuclear magnetic resonance, mass spectrometry and elemental analysis.

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Abstract

The invention discloses a synthesis method of 1-((3-(5-nitro-2-furyl)allylidene)amino) hydantoin. The synthesis method is characterized by including: taking 5-nitrofuranacrolein and propyl aminohydantoin as main raw materials, allowing one-step condensation reaction to prepare a target compound crude product, and refining and purifying N, N-dimethylformamide to obtain 1-((3-(5-nitro-2-furyl)allylidene)amino) hydantoin, wherein a chemical reaction formula is shown as follows. Compared with reported methods, the synthesis method has the advantages that reaction path is short, process is simple and convenient, the raw materials are easy to get, generation of a pollution byproduct-aldehyde during synthesis is avoided, and the method is high in yield, low in cost, few in three wastes and environment-friendly, and reaction conversion rate reaches 98%.

Description

technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical intermediates, and in particular relates to a synthesis method of 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin. Background technique [0002] 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin, the CAS number is [1672-88-4], the molecular structure is shown in the figure below: [0003] [0004] 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin is a class of nitrofuran derivatives, an anti-infective drug, mainly used for urinary tract infections, Its antibacterial properties are similar to those of nitrofurantoin and nitrofurandine. 1-((3-(5-nitro-2-furyl)allylidene)amino)hydantoin has a wide antibacterial spectrum and has antibacterial effects on most Gram-positive and Gram-negative bacteria, such as Staphylococcus aureus , Escherichia coli, Staphylococcus albus and Streptococcus pyogenes. It is clinically used for urinary system infection caused by sensitive bacte...

Claims

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Application Information

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IPC IPC(8): C07D405/12
CPCC07D405/12
Inventor 徐来隋宁
Owner 黄石法姆药业股份有限公司
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