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Synthetic method of double-labeling nitrofurazone-(13C, 15N2)

A technology of nitrofuracil and a synthesis method, applied in the field of preparation of organic compounds, can solve the problems of difficulty in introducing isotope labels, a large amount of waste acid, etc., and achieve the effects of high yield and simple process

Inactive Publication Date: 2012-11-07
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Adopt the above method to synthesize double-labeled nitrofurazone-( 13 C, 15 N 2 ) have deficiencies, are difficult to introduce isotope labeling, and use and produce a large amount of waste acid

Method used

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  • Synthetic method of double-labeling nitrofurazone-(13C, 15N2)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 250ml three-neck flask equipped with a thermometer and a reflux condenser, add 6.3 grams of double-labeled urea-( 13 C, 15 N 2 ) and 20 grams of hydrazine hydrate, stirred, heated to 70°C, and reacted for 4 hours. The insoluble matter was removed by filtration to obtain a semicarbazide solution.

[0021] Add 50ml of ethanol to the semicarbazide solution, then sequentially add 24.3 grams of 5-nitrofurfural diethyl ester and 5ml of 6mol / L sulfuric acid, stir, and heat to 50. °C, react for 6 hours. After cooling, it was filtered to obtain a white solid, which was recrystallized from DMF. After refining, the product was vacuum-dried solid for 4 hours, that is, 12.5 grams of double-labeled nitrofurazone-( 13 C, 15 N 2 ). The total yield of the reaction was 62.2% (with double-labeled urea-( 13 C, 15 N 2 )count), 13 C abundance 98.1%, 15 N abundance 98.5%, purity 99.3%.

Embodiment 2

[0023] In a 250ml three-neck flask equipped with a thermometer and a reflux condenser, add 6.3 grams of double-labeled urea-( 13 C, 15 N 2 ) and 50 grams of hydrazine hydrate, stirred, heated to 50°C, and reacted for 10 hours. The insoluble matter was removed by filtration to obtain a semicarbazide solution.

[0024] Add 200ml of methanol to the semicarbazide solution, then add 72.9g of 5-nitrofurfural diethyl ester and 1ml of 12mol / L concentrated hydrochloric acid in sequence, stir, heat to 20°C, and react for 1 hour. After cooling, it was filtered to obtain a white solid, which was recrystallized from DMF. After refining, the product was vacuum-dried solid for 4 hours, that is, 13.5 grams of double-labeled nitrofurazone-( 13 C, 15 N 2 ). The total reaction yield was 67.2% (with double-labeled urea-( 13 C, 15 N 2 )count), 13 C abundance 98.2%, 15 N abundance 98.3%, purity 99.2%.

Embodiment 3

[0026] In a 250ml three-neck flask equipped with a thermometer and a reflux condenser, add 6.3 grams of double-labeled urea-( 13 C, 15 N 2 ) and 30 grams of hydrazine hydrate, stirred, heated to 100°C, and reacted for 6 hours. The insoluble matter was removed by filtration to obtain a semicarbazide solution.

[0027] Add 20ml of butanol to the semicarbazide solution, then sequentially add 48.6g of 5-nitrofurfural diethyl ester and 8ml of 8mol / L hydrofluoric acid, stir, heat to 80°C, and react for 3 hours. After cooling, it was filtered to obtain a white solid, which was recrystallized from DMF. After refining, the product was vacuum-dried solid for 4 hours, that is, 13.2 grams of double-labeled nitrofurazone-( 13 C, 15 N 2 ). The total reaction yield was 65.7% (with double-labeled urea-( 13 C, 15 N 2 )count), 13 C abundance 98.3%, 15 N abundance 98.2%, purity 99.1%.

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Abstract

The invention relates to a synthetic method of double-labeling nitrofurazone-(13C, 15N2). The synthetic method includes the following steps: (1) adding hydrazine hydrate and double-labeling urea-(13C, 15N2) in a reactor according to molar ratio of 2-5:1, stirring, heating to 50-100 DEG C, reacting for 4-10 hours, filtering to remove undissolved substances, and obtaining semicarbazide solution; (2) adding solvent, 5-nitro furfural diethyl ester and strong acid in the semicarbazide solution, stirring, heating to 20-80 DEG C, reacting for 1-6 hours, cooling, filtering, obtaining whole solid, using dimethyl formamide (DMF) to perform recrystallization, drying purified solid products in vacuum mode for 4 hours, and obtaining the double-labeling nitrofurazone-(13C, 15N2). Compared with the prior art, the synthetic method of the double-labeling nitrofurazone-(13C, 15N2) can effectively and accurately detect content of nitrofurazone in feed and food and is simple, practicable and suitable for batch production.

Description

technical field [0001] The present invention relates to the preparation method of the organic compound of stable isotope label, relate in particular to a kind of double labeled nitrofurazone-( 13 C, 15 N 2 ) organic synthesis method. Background technique [0002] Furacillin is a synthetic nitrofuran broad-spectrum antibacterial drug. It mainly interferes with the oxidoreductase system in bacteria to disturb the metabolism of bacteria, so as to achieve the effect of sterilization and antisepsis. It was widely used as an animal feed additive in the early days, but it was later found to have strong cell mutagenicity and animal carcinogenic toxicity (Zhu Weixia, Liu Yafeng. Research progress in the detection of nitrofuran drug residues in animal foods[J]. Advances in Veterinary Medicine , 2010(2): 99-102.), so it was completely banned in feed production (Zhang Qing, Wang Chao, Wang Xing, etc. Simultaneous determination of nitrofurantoin and furazolidone in cosmetics by high p...

Claims

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Application Information

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IPC IPC(8): C07D307/73
Inventor 徐建飞杜晓宁王伟郑波张彰
Owner SHANGHAI RES INST OF CHEM IND
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