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Synthesizing process of nitro iodo phenol cyanide

A technology of nitroiodophenol nitrile and synthesis method is applied in chemical instruments and methods, preparation of carboxylic acid nitrile, preparation of organic compounds, etc. The effect of reducing environmental pollution, reducing production costs and simplifying production operations

Inactive Publication Date: 2009-06-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic method uses iodine as the iodination reagent with high cost, difficult operation, serious environmental pollution, hydrogen peroxide is easy to decompose, dangerous, and the total yield is low

Method used

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  • Synthesizing process of nitro iodo phenol cyanide
  • Synthesizing process of nitro iodo phenol cyanide
  • Synthesizing process of nitro iodo phenol cyanide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of p-hydroxybenzonitrile

[0034] Add p-hydroxybenzaldehyde (6.10g, 0.05mol), hydroxylamine hydrochloride (4.17g, 0.06mol), sodium formate (6.24g, 0.06mol) and formic acid (20ml) successively into a 250ml three-necked flask, and reflux for 30min. Recover most of the formic acid by distillation under reduced pressure. After the remaining liquid is cooled, add 50g / L sodium hydroxide solution dropwise to adjust the pH value to 5-6. White crystals are precipitated. After filtering, washing and drying, 2.85g of the product is obtained. Add chlorine to the filtrate. After the sodium chloride was saturated, another 0.15 g of crystals was precipitated, and the total yield was 50.1%. The purity measured by gas chromatography is 98.9%; m.p.112.0~112.6°C (literature value 113°C).

[0035] Elemental Analysis C 7 h 5 NO, measured value (calculated value), %: C 70.55 (70.58), H 4.08 (4.23), N11.56 (11.76); IR (KBr tablet).cm -1 : 3413, 2233, 1615, 15...

Embodiment 2

[0036] Embodiment 2: the preparation of nitrophenol nitrile

[0037] Add p-hydroxybenzonitrile (5.95g, 0.05mol), sodium periodate (2.14g, 0.01mol), sodium chloride (5.85g, 0.1mol), potassium iodide (8.3g, 0.05 mol), acetic acid (150ml), stirred at 50°C for 30 minutes, and the product liquid was white at this time; then sodium nitrite (3.45g, 0.05mol) was added, and the temperature was raised to 80°C for 3h. Recrystallize from ethanol solution with a volume ratio of ethanol to water of 1:10 to obtain 13.78 g of the product, with a yield of 30%. m.p.136.9-137.5°C (literature value 137-138°C).

[0038] Elemental Analysis, C 7 h 3 IN 2 o 3 , measured value (calculated value), %: C 29.12 (28.99), H 1.27 (1.04), N 9.60 (9.66).IR (KBr tablet), cm -1 : 3415, 2233, 1606, 1536, 1351, 1251, 1128, 903, 729; MS (m / z): 290 (M -), 273(290-OH), 244(290-NO 2 ), 146(290-OH-I), 117(290-NO 2 -I).

Embodiment 3

[0039] Embodiment 3: the preparation of p-hydroxybenzonitrile

[0040] Add p-hydroxybenzaldehyde (6.10g, 0.05mol), hydroxylamine hydrochloride (4.17g, 0.06mol), sodium formate (6.24g, 0.06mol) and formic acid (40ml) successively into a 250ml three-necked flask, and reflux for 30min. Recover most of the formic acid by distillation under reduced pressure. After the remaining liquid is cooled, add 50g / L sodium hydroxide solution dropwise to adjust the pH value to 5-6. White crystals are precipitated. After filtering, washing and drying, 4.85g of the product is obtained. Add chlorine to the filtrate. After the sodium chloride was saturated, another 0.42 g crystals were precipitated, and the total yield was 88.6%. The purity measured by gas chromatography is 98.9%; m.p.112.0~112.6°C (literature value 113°C).

[0041] Elemental Analysis C 7 h 5 NO, measured value (calculated value), %: C 70.55 (70.58), H 4.08 (4.23), N11.56 (11.76); IR (KBr tablet).cm -1 : 3413, 2233, 1615, 1586...

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Abstract

This invention involves a nitroxinil synthesis way, including the following steps: put P-hydroxy benzonitrile or P-hydroxy benzaldehyde (PHB), oxygenated iodate such as sodium periodate, alkali metal iodide such as potassium iodide, alkali metal chlorides such as sodium chloride in acetic acid, at 10 to 150deg C for 0.1 to 6hours reaction, then add sodium nitrite at 10 to 150 deg C for 1 to 10hours reaction, through post-treatment obtain nitroxinil . This invention provides a 'one pot method' to synthesis nitroxinil. It condense the original traditional three-step synthesis process to two steps to simplify and shorten the synthesis routes, lower raw material costs, simplify operations, improve product yield and reduced waste generation.

Description

(1) Technical field [0001] The invention relates to a new method for synthesizing the liver fluke drug niclofenac. (2) Background technology [0002] Nitrophenonitrile (4-hydroxyl-3-iodo-5-nitrobenzonitrile, Nitroxynil) is a new drug for preventing and treating cattle and sheep Fasciola hepatica infection. It was successfully developed by the French Rhone Merieux Institute in the 1980s. Since 1987, our country has been relying on imports, which limits its wide application in our country to a certain extent. Fascioliasis hepatica is widely distributed all over the world and has caused serious economic losses to many countries. Japan alone loses about 33 billion yen per year. This disease is regionally prevalent in various provinces and autonomous regions of my country. Ningxia, Qinghai, Gansu, Xinjiang and other provinces and regions are even more rampant, and the economic loss of animal husbandry caused by the disease reaches hundreds of millions of yuan every year. Therefo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/00C07C255/53
Inventor 裴文陶金海孙莉
Owner ZHEJIANG UNIV OF TECH
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