CN102093337A - Preparation method of acetyl benzimidazole pyridine salt - Google Patents
Preparation method of acetyl benzimidazole pyridine salt Download PDFInfo
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- CN102093337A CN102093337A CN2010105735701A CN201010573570A CN102093337A CN 102093337 A CN102093337 A CN 102093337A CN 2010105735701 A CN2010105735701 A CN 2010105735701A CN 201010573570 A CN201010573570 A CN 201010573570A CN 102093337 A CN102093337 A CN 102093337A
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Abstract
The invention discloses a preparation method of acetyl benzimidazole pyridine salt. The method comprises the following steps of: adding iodine, a pyridine compound and 1,4-dioxane into a reactor; rising the temperature to 55-60 DEG C under the protection of inert gas; adding 3-substitute-2-acetyl benzimidazole, and then rising the temperature to 95-105 DEG C; continuing reacting for 2-3 hours, and decompressing to remove the solvent; dispersing the residue into pyridine, and cooling to 0-10 DEG C; carrying out pump filtering on solid; and washing an obtained filter cake with chloroform and diethyl ether to obtain the acetyl benzimidazole pyridine salt. The preparation method has the advantages of moderate reaction condition, simpleness of operation, easiness of obtaining raw materials and high total productivity.
Description
Technical field
The invention belongs to the organic synthesis field, relate to a kind of preparation method of acetyl benzo Imidazopyridine salt compounded of iodine specifically.
Background technology
Benzimidazoles compound is a kind of heterogeneous ring compound that contains two nitrogen-atoms, can be used as pharmaceutical intermediate, people and animals' anthelmintic drug and sterilant and the fruit antistaling agent of Citrus fruit.Its some metal complexes has sterilization, anticancer isoreactivity.And metal complexes such as its copper zinc has special catalytic property, has important effect aspect the simulation of metalloenzyme.Because its structural performance, physiologically active, reactive behavior and other excellent characteristic, the synthetic and applied research of benzoglyoxaline and derivative thereof in decades never is interrupted, so far very active still.And the compound that contains pyridine nucleus also extensively is present in natural compounds and the supramolecular structure. therefore, the synthetic polysubstituted pyridine that contains benzoglyoxaline has great importance.Forefathers adopt cinchomeronic acid and O-Phenylene Diamine prepared in reaction mostly, but this method raw material costliness, reaction is complicated, and yield is not high.
Summary of the invention
Technical problem to be solved by this invention is: provide a kind of raw material cheaply to be easy to get, reaction is simple, the preparation method of the acetyl benzo Imidazopyridine salt compounded of iodine that yield is high.
For solving the problems of the technologies described above, the technical solution used in the present invention is: a kind of preparation method of acetyl benzo Imidazopyridine salt compounded of iodine, and above preparation process is as follows:
The preparation method of acetyl benzo Imidazopyridine salt compounded of iodine, synthesis step comprises:
In reactor, add iodine, pyridine compounds and their and 1, the 4-dioxane, under protection of inert gas, be warming up to 55 ~ 60 ℃, after wherein adding 3-replacement-2-ethanoyl benzo imidazoles, be warming up to 95 ~ 105 ℃ and continue reaction 2 ~ 3 h, removal of solvent under reduced pressure, residue dispersion is in pyridine, be cooled to 0 ~ 10 ℃, the suction filtration solid, filter cake washs with chloroform and ether;
Wherein, the mol ratio of 3-replacement 2-ethanoyl benzo imidazoles and pyridine compounds and their and iodine is 1:2.5 ~ 3:2 ~ 3; Pyridine compounds and their is a pyridone, alkyl pyridine or aminopyridine; It is 2-ethanoyl benzo imidazoles that 3-replaces 2-ethanoyl benzo imidazoles, 3-methyl-2-ethanoyl benzo imidazoles or 3-ethyl-2-ethanoyl benzo imidazoles; Used rare gas element is a nitrogen, a kind of or several combination arbitrarily in helium or the argon gas.
Beneficial effect of the present invention: a kind of reaction conditions gentleness is provided, and simple to operate, raw material is easy to get, and the preparation method of the high acetyl benzo Imidazopyridine salt compounded of iodine of overall yield.
Embodiment
Describe specific embodiments of the present invention below in detail.
Embodiment 1:
In reactor, add iodine (4.9 g; 19.3 mmol), pyridine (2 mL; 24.1 mmol) and 1; 4-dioxane (25 mL); under protection of inert gas, be warming up to 55 ~ 60 ℃; after wherein adding 2-ethanoyl benzo imidazoles (1.5 g, 9.65 mmol), be warming up to 100 ~ 110 ℃; continue reaction 1 ~ 1.5 h; removal of solvent under reduced pressure, residue dispersion is cooled to 0 ~ 10 ℃ in pyridine (10 mL); suction filtration; filter cake washs with chloroform (10 mL) and ether (10 mL), and product is dried to constant weight, yield: 87.3%.
Embodiment 2:
In reactor, add iodine (172.2 g; 678.5 mmol), 2-aminopyridine (56.7 g; 602.8mmol) and 1; 4-dioxane (800 mL); under the helium protection, be warming up to 55 ~ 60 ℃; after wherein adding 3-methyl-2-ethanoyl benzo imidazoles (37.5 g, 251.3 mmol), be warming up to 95 ~ 105 ℃; continue reaction 2 h; removal of solvent under reduced pressure, residue dispersion is cooled to 0 ~ 10 ℃ in pyridine (250 mL); suction filtration; filter cake washs with chloroform (50 mL) and ether (50 mL), and product is dried to constant weight, yield: 84.6%.
Embodiment 3:
In reactor, add iodine (302.7 g; 1.19 mol), 4-pyridone (113.4 g; 1.19 mol) and 1; 4-dioxane (1200 mL); under argon shield, be warming up to 55 ~ 60 ℃; after wherein adding 3-ethyl-2-ethanoyl benzo imidazoles (74.8 g, 397.5 mmol), be warming up to 95 ~ 105 ℃; continue reaction 2.5 h; removal of solvent under reduced pressure, residue dispersion is cooled to 0 ~ 10 ℃ in pyridine (400 mL); suction filtration; filter cake washs with chloroform (50 mL * 2) and ether (50 mL * 2), and product is dried to constant weight, yield: 82.4%.
Claims (5)
1. the preparation method of acetyl benzo Imidazopyridine salt compounded of iodine, synthesis step comprises:
In reactor, add iodine, pyridine compounds and their and 1; the 4-dioxane; under protection of inert gas, be warming up to 55 ~ 60 ℃; after wherein adding 3-replacement-2-ethanoyl benzo imidazoles, be warming up to 95 ~ 105 ℃ and continue reaction 2 ~ 3 h, removal of solvent under reduced pressure; residue dispersion is in pyridine; be cooled to 0 ~ 10 ℃, the suction filtration solid, filter cake washs with chloroform and ether.
2. the preparation method of a kind of acetyl benzo Imidazopyridine salt compounded of iodine according to claim 1 is characterized in that, the mol ratio that 3-replaces 2-ethanoyl benzo imidazoles and pyridine compounds and their and iodine is 1:2.5 ~ 3:2 ~ 3.
3. the preparation method of a kind of acetyl benzo Imidazopyridine salt compounded of iodine according to claim 1 is characterized in that pyridine compounds and their is pyridone, alkyl pyridine or aminopyridine.
4. the preparation method of a kind of acetyl benzo Imidazopyridine salt compounded of iodine according to claim 1 is characterized in that it is 2-ethanoyl benzo imidazoles that 3-replaces 2-ethanoyl benzo imidazoles, 3-methyl-2-ethanoyl benzo imidazoles or 3-ethyl-2-ethanoyl benzo imidazoles.
5. the preparation method of a kind of acetyl benzo Imidazopyridine salt compounded of iodine according to claim 1 is characterized in that used rare gas element is a nitrogen, a kind of or several combination arbitrarily in helium or the argon gas.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010573570 CN102093337B (en) | 2010-12-06 | 2010-12-06 | Preparation method of acetyl benzimidazole pyridine salt |
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| CN 201010573570 CN102093337B (en) | 2010-12-06 | 2010-12-06 | Preparation method of acetyl benzimidazole pyridine salt |
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| CN102093337A true CN102093337A (en) | 2011-06-15 |
| CN102093337B CN102093337B (en) | 2013-01-23 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102964374A (en) * | 2012-11-28 | 2013-03-13 | 玉林师范学院 | Benzimidazole pyridine complex and method for preparing same |
-
2010
- 2010-12-06 CN CN 201010573570 patent/CN102093337B/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 景崤壁 等: "新型含有苯并咪唑取代基的多取代吡啶类化合物及其配合物的合成与表征", 《有机化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102964374A (en) * | 2012-11-28 | 2013-03-13 | 玉林师范学院 | Benzimidazole pyridine complex and method for preparing same |
| CN102964374B (en) * | 2012-11-28 | 2015-10-28 | 玉林师范学院 | A kind of benzoglyoxaline pyridines title complex and preparation method thereof |
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| CN102093337B (en) | 2013-01-23 |
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Owner name: ZHOU YULIAN Free format text: FORMER OWNER: ZHANGJIAGANG TIANYOU NEW MATERIAL TECHNOLOGY CO., LTD. Effective date: 20121206 |
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Effective date of registration: 20121206 Address after: Suzhou City, Jiangsu province 215636 Daxin Town, Zhangjiagang city along the Yangtze River Road on the north side of Taihua chemical technical room Applicant after: Zhou Yulian Address before: Zhangjiagang City Daxin Town old dam village in Suzhou City, Jiangsu province 215636 Zhangjiagang field by the new Mstar Technology Ltd Applicant before: Zhangjiagang Tianyou New Material Technology Co., Ltd. |
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