Synthesis method of 2-nitroethenyl thiophene

A technology of nitroethylene and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of large amount of nitromethane and high purification cost, and achieve the effects of increasing yield, shortening reaction time, and promoting reaction

Inactive Publication Date: 2014-03-26
山西瑞谱德科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that the amount of nitromethane is too large (nitromethane: 2-thiophene formaldehyde molar ratio = 56:1), and the cost of product purification by silica gel column is high

Method used

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  • Synthesis method of 2-nitroethenyl thiophene
  • Synthesis method of 2-nitroethenyl thiophene
  • Synthesis method of 2-nitroethenyl thiophene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Put 11.2g (0.1mol) 2-thiophene carboxaldehyde, 7.3g (0.12mol) nitromethane, 4ml acetonitrile solution of 0.9g (0.01mol) β-alanine in the reaction bottle, 60ml N,N-di Methylformamide, 90°C ultrasonic radiation (100W, 40kHz) for 1h, cooled, distilled off acetonitrile, filtered, concentrated, the residue was recrystallized to give 14.6g of 2-nitroethylenethiophene (yield 94%), yellow crystals, m .p79~80℃, content 99.2% (GC). β-alanine recovery 0.75g, can be reused.

Embodiment 2

[0032] Put 11.2g (0.1mol) 2-thiophenecarbaldehyde, 6.1g (0.10mol) nitromethane, 4ml acetonitrile solution of 0.9g (0.01mol) β-alanine in the reaction flask, 60ml N,N-di Methylformamide, 90°C ultrasonic radiation (100W, 40kHz) for 1h, cooled, distilled off acetonitrile, filtered, concentrated, recrystallized to give 13.3g of 2-nitrovinylthiophene (yield 86%), yellow crystal, m.p 79 ~80°C, content 99.2% (GC). β-alanine recovery 0.75g, can be reused.

Embodiment 3

[0034] Put 11.2g (0.1mol) 2-thiophene carboxaldehyde, 8.5g (0.14mol) nitromethane, 4ml acetonitrile solution of 0.9g (0.01mol) β-alanine in the reaction bottle, 60ml N,N-di Methylformamide, 90°C ultrasonic radiation (100W, 40kHz) for 1h, cooled, distilled off acetonitrile, filtered, concentrated, and recrystallized to give 14.7g of 2-nitroethylenethiophene (yield 95%), yellow crystal, m.p 79 ~80°C, content 99.1% (GC). 0.74g of β-alanine is recovered and can be reused.

[0035] In the above examples, the method of the present invention adds 2-thiophene formaldehyde, nitromethane, β-alanine solution dissolved in acetonitrile, and solvent into the reaction flask, and reacts with ultrasonic radiation (100W, 40kHz) at 90°C for 1 hour, and after post-treatment, the The product 2-nitroethylenethiophene was obtained, and the recovery of β-alanine was more than 82%, which could be reused. Compared with the existing technology, the process has the characteristics of simple operation, ...

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Abstract

The invention relates to a synthesis method of 2-nitroethenyl thiophene. The synthesis method comprises the following steps: adding 2-thiophenecarboxaldehyde, nitromethane, beta-alanine dissolved with acetonitrile and a solvent into a reaction flask, reacting for 1h under unltrasound irradiation; after reaction, removing acetonitrile, filtering out beta-alanine, concentrating, and recrystallizing residues to obtain 2-nitroethenyl thiophene. The synthesis method provided by the invention has the characteristics of low cost, simpleness and convenience in operation, high yield and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 2-nitroethylenethiophene, in particular to a method for synthesizing 2-nitroethylenethiophene through one-step reaction using 2-thiophene formaldehyde and nitromethane as raw materials. Background technique [0002] 2-Nitroethylenethiophene is an intermediate in some pharmaceutical and chemical industries, and can be used to synthesize 2-thienylethylamine, ticlopyridine, clopidogrel, prasugrel, etc. Its structural formula is as follows: [0003] [0004] The synthesis method of 2-nitroethylenethiophene reported in open literature is mainly prepared by reacting 2-thiophenecarbaldehyde with nitromethane, but the reaction conditions are somewhat different. [0005] Existing public document US4906756 reports, puts 2-thiophene formaldehyde, nitromethane, methyl alcohol into reaction flask, drips sodium hydroxide solution, after reaction is finished, pours into hydrochloric acid solution to obtain 2-nitro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/12
Inventor 邢俊德苗茂谦张照昱李强
Owner 山西瑞谱德科技有限公司
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