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Synthesis method of 2-nitroethenyl thiophene

A technology of nitroethylene and a synthesis method, applied in directions such as organic chemistry, can solve the problems of high purification cost and large amount of nitromethane, and achieve the effects of shortening reaction time, improving yield, and using less amount

Inactive Publication Date: 2012-10-03
山西瑞谱德科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 present invention involves a synthesis method of 2-nitroceleneneys, especially a synthesis method of 2-nitrotinyethylene phenea with 2-pneumatic formaldehyde and nitrotine as the raw material. Background technique [0002] 2-nitrocelenenesses are the intermediates of some pharmaceutical chemicals, which can be used to synthesize 2-pneumophyte, deoxylpyamidine, clopidogrera, Praogra, etc. The structure is as follows: [0003] [0004] The synthesis method of 2-nitrotinylinophene reported by the public literature is mainly obtained by the reaction of 2-pneumatum formaldehyde and nitro, but the response conditions are different. [0005] The existing public literature US4906756 reports that 2-pneumatic formaldehyde, nitro, methanol is placed in a reaction bottle, dripping the sodium hydroxide solution, and the response was poured.Formula is: [0006] [0007] This method places the raw material 2-dens with formaldehyde, nitrochine, and methanol into th...

Claims

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Application Information

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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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