CN109096205A - A kind of synthetic method of benzimidazoles compound - Google Patents
A kind of synthetic method of benzimidazoles compound Download PDFInfo
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- CN109096205A CN109096205A CN201811181219.0A CN201811181219A CN109096205A CN 109096205 A CN109096205 A CN 109096205A CN 201811181219 A CN201811181219 A CN 201811181219A CN 109096205 A CN109096205 A CN 109096205A
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- synthetic method
- phenylenediamine
- substituted
- benzimidazoles compound
- carnitine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
Abstract
The invention discloses a kind of synthetic method of benzimidazoles compound, the synthetic route of the synthetic method are as follows:
Description
Technical field
The invention belongs to organic heterocyclic molecules to synthesize field, and in particular to a kind of synthesis side of benzimidazoles compound
Method.
Background technique
Benzimidazoles compound is a kind of very important organic heterocyclic molecule, with multiple biological activities and medicine
Reason activity, such as: blood coagulation, anticancer, spasmolysis, antiallergy etc., meanwhile, benzimidizole derivatives are also the important of many natural products
Component units.Therefore, in recent years, people are more and more deep to the research of benzimidizole derivatives, it has also become Synthetic Organic Chemistry
The hot spot of research field.
In the prior art, the common method of synthesizing benzimidazole derivative is that o-phenylenediamine and aromatic aldehyde dehydration condensation is anti-
It should be made.Usually require strong acid condition, it is sometimes desirable to which very high reaction temperature, yield are not ideal enough.Common synthetic method is
Oxidant is added, such as nitrobenzene, 1,4-benzoquinone, chloro- 5, the 6- dicyanoquinone (DDQ) of 2,3- bis-, manganese dioxide and sodium thiosulfate
Deng.These oxidizer catalytic synthesizing benzimidazoles usually require to carry out at high temperature, and condition is harsh, complicated for operation, product
It post-processes cumbersome.There are also synthesize benzo miaow as catalyst using metal indium compound, rare earth metal ytterbium compound, tannic acid etc.
Azole compounds, although o-phenylenediamine and fragrant aldehyde reaction generation benzimidazoles compound can be effectively catalyzed, more or less
There are some problems, for example expensive catalyst, catalyst preparation difficulty, severe reaction conditions, post-processing operation is cumbersome and urges
Agent can not recycle and reuse, catalyst remains harmfulness etc..
Therefore, need to develop a kind of synthesis of benzimidazoles compound that combined coefficient is high, easy to operate, environmentally protective
Method.
Summary of the invention
In view of the deficiencies of the prior art, the object of the present invention is to provide a kind of synthetic method of benzimidazoles compound,
The method has the characteristics that combined coefficient is high, easy to operate, environmentally protective.
The technical solution adopted by the present invention is that: a kind of synthetic method of benzimidazoles compound,
The synthetic route of the synthetic method are as follows:
For the present invention using L-carnitine as catalyst, it is a kind of slimming drugs, relatively safety low-poison.Meanwhile based on a left side
Quaternary ammonium salt N cation and carboxyl anion structure in rotation carnitine molecule is in its catalytic process, when forming transition state intermediate
Compare smoothly, eventually pass through oxidation and obtain target molecule, Catalysis Principles are as follows:
The synthetic method the following steps are included:
1) substituted o-phenylenediamine (I), aromatic aldehyde (II) and L-carnitine are added in solvent, carry out heating reaction, obtains
To crude product；
2) filtration of crude product for obtaining step 1), collects solid matter, and drying obtains benzimidazoles compound
(Ⅲ)；
The Ar of the aromatic aldehyde be it is o-, m- and/or contraposition on have substituent group phenyl ring, the substituent group include halogen,
Methoxyl group and nitro；
The R of the substituted o-phenylenediamine includes hydrogen and nitro.
Preferably, the synthetic method further includes that the benzimidazoles compound after drying is carried out weight after step 2)
The step of crystallization.
More specifically, a kind of synthetic method of benzimidazoles compound the following steps are included:
1) substituted o-phenylenediamine, aromatic aldehyde and L-carnitine are added in solvent, carry out heating reaction, is slightly produced
Object；
2) filtration of crude product for obtaining step 1), collects solid matter, and drying obtains benzimidazole with ethyl alcohol recrystallization
Class compound.
Preferably, in step 1), the molar ratio of substituted o-phenylenediamine and aromatic aldehyde is 1-3:1-3.It is furthermore preferred that replacing adjacent
The molar ratio of phenylenediamine and aromatic aldehyde is 1:1.
Preferably, in step 1), the molar ratio of substituted o-phenylenediamine and L-carnitine is 1:0.05-0.15.It is furthermore preferred that
The molar ratio of substituted o-phenylenediamine and L-carnitine is 1:0.1.
Preferably, in step 1), solvent is selected from n-hexane, hexamethylene, 1,2- dichloroethanes, ethyl alcohol, chloroform and water
One of or it is a variety of.It is furthermore preferred that solvent is 95% ethyl alcohol in step 1).
Preferably, in step 1), the molal quantity of substituted o-phenylenediamine and the volume ratio of solvent are 1mmol:3-10mL.It is more excellent
Choosing, the molal quantity of substituted o-phenylenediamine and the volume ratio of solvent are 1mmol:5mL.
Preferably, in step 1), the temperature for heating reaction is 25-80 DEG C, and the time for heating reaction is 1-4h.More preferably
, the temperature for heating reaction is 60 DEG C, and the time for heating reaction is 2h.
Preferably, in step 2), the temperature of drying is 60-120 DEG C, and the time of drying is 1-5h.More specifically, drying
Temperature is 90 DEG C, and the time of drying is 1h；Or the temperature of drying is 100 DEG C, the time of drying is 2h.
Compared with prior art, the present invention having the following beneficial effects:
1. substituted o-phenylenediamine, aromatic aldehyde and L-carnitine are creatively obtained benzo miaow by the present invention in a heated condition
Azole compounds, for the synthetic method using substituted o-phenylenediamine and aromatic aldehyde as starting material, preparation is simple, easy to operate,
In addition to final product, a series of intermediate in conversion processes is not necessarily to separate and purify, and the catalytic amount used is few, saves
The input amount of cost and labour, succinctly efficiently preparing benzimidazoles compound provides a kind of important means to be green.
2. the Catalysis Principles of catalyst L-carnitine is that quaternary ammonium salt N cation and carboxyl anion structure are urged at it in molecule
During change, formed transition state intermediate when it is more smooth, eventually pass through oxidation and obtain target molecule.The catalyst is commercialization
Product, source are easy to get, cheap, and reaction condition is mildly controllable, and combined coefficient is high, can be used repeatedly, and post-processing is simple.
Also, benzimidazoles compound is important clinical medicine, and the residual of catalyst may bring harm to patient.And this hair
Catalyst L-carnitine, is generally acknowledged fat-reducing nutrient complementary goods, can take safely used by bright, even if still having after post-processing
A small amount of L-carnitine residual, will not bring harm to patient body.
3. the present invention program starting material is cheap and easy to get, reaction condition is relatively mild, combined coefficient height and post-processing operation
Simplicity, the yield of synthesizing benzimidazole class compound of the present invention are 90-98%, purity 92-99%, have good practical valence
Value and socio-economic efficiency have good reference to the process exploitation of similar product and downstream product.
Specific embodiment
Below with reference to embodiment, the present invention will be further described.
Embodiment 1
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (108mg, 1.0mmo1), p-chlorobenzaldehyde (141mg, 1.0mmo1) and L-carnitine
(16.1mg, 0.1mmol) is added in 95% ethyl alcohol of 5mL, and under electromagnetic agitation, 2h is reacted in 60 DEG C of heating, obtains crude product；
2) filtration of crude product for obtaining step 1) dries 1h at a temperature of 90 DEG C, and it is solid to obtain white with ethyl alcohol recrystallization
Body, yield 97%, purity 99%.
Product is subjected to magnetic resonance detection and essential element analysis, data are as follows:
1H-NMR(400MHz,DMSO-d6): δ 13.03 (s, 1H), 8.23 (d, 2H, J=8.5Hz), 7.70-7.63 (m,
3H), 7.55 (d, 1H, J=7.2Hz), 7.26-7.23 (m, 2H)；
13C NMR(100MHz,DMSO-d6):δ149.8,143.5,134.5,134.3,129.0,128.7,128.1,
122.6,121.8,118.7,111.3；
Anal.Calcd.for C13H9ClN2:C 68.28,H 3.97,N 12.25.Found:C 68.23,H 4.12,N
12.28。
Magnetic resonance detection and essential element analysis the result shows that, obtained product be 2- (4- chlorphenyl) -1H- benzo
[d] imidazoles.
Embodiment 2
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by 4-nitro-o-phenylenediamine (153mg, 1.0mmo1), p-chlorobenzaldehyde (141mg, 1.0mmo1) and L-carnitine
(16.1mg, 0.1mmol) is added in 95% ethyl alcohol of 5mL, and under electromagnetic agitation, 2h is reacted in 60 DEG C of heating, obtains crude product；
2) filtration of crude product for obtaining step 1) dries 2h at a temperature of 60 DEG C, and it is solid to obtain yellow with ethyl alcohol recrystallization
Body, yield 98%, purity 99%.
Product is subjected to magnetic resonance detection and essential element analysis, data are as follows:
1H-NMR(400MHz,DMSO-d6): δ 13.66 (s, 1H), 8.81 (s, 1H), 8.12 (d, J=9.0Hz, 1H),
8.01 (d, J=9.0Hz, 1H), 7.52 (d, J=9.0Hz, 2H), 7.43 (d, J=9.0Hz, 2H)；
13C NMR(100MHz,DMSO-d6)δ158.4,151.1,135.9,135.2,133.3,131.6,129.9,
125.0,124.4,113.2,112.8；
Anal.Calcd.for C13H8ClN3O2:C 57.05,H 2.95,N 15.35.Found:C 57.16,H 2.76,
N 15.33。
Magnetic resonance detection and essential element analysis the result shows that, obtained product be 2- (4- chlorphenyl) -5- nitro -
1H- benzo [d] imidazoles.
Embodiment 3
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (108mg, 1.0mmo1), P-methoxybenzal-dehyde (136mg, 1.0mmo1) and L-carnitine
(16.1mg, 0.1mmol) is added in 95% ethyl alcohol of 5mL, and under electromagnetic agitation, 1h is reacted in 60 DEG C of heating, obtains crude product；
2) filtration of crude product for obtaining step 1) dries 3h at a temperature of 70 DEG C, and it is solid to obtain white with ethyl alcohol recrystallization
Body, yield 95%, purity 99%.
Product is subjected to magnetic resonance detection and essential element analysis, data are as follows:
1H NMR (400MHz, DMSO-d6): δ 12.75 (s, 1H), 8.09 (d, 2H, J=8.7Hz), 7.55 (m, 2H),
7.19-7.16 (m, 2H), 7.10 (d, 2H, J=8.8Hz), 3.83 (s, 3H)；
13C NMR(100MHz,DMSO-d6): δ 160.3,151.0,143.4,134.7,127.7,122.3,121.8,
121.4,118.1,114.0,110.8,55.1；
Anal.Calcd.for C14H12N2O:C 74.98,H 5.39,N 12.49.Found:C 74.79,H 5.21,N
12.46。
Magnetic resonance detection and essential element analysis the result shows that, obtained product be 2- (4- methoxyphenyl) -1H- benzene
And [d] imidazoles.
Embodiment 4
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (108mg, 1.0mmo1), p-chlorobenzaldehyde (141mg, 1.0mmo1) and L-carnitine
(16.1mg, 0.1mmol) is added in 5mL hexamethylene, and under electromagnetic agitation, 1h is reacted in 80 DEG C of heating, obtains crude product；
2) filtration of crude product for obtaining step 1) dries 4h at a temperature of 60 DEG C, obtains product 2- (4- chloro phenyl)-
1H- benzo [d] imidazoles, yield 90%, purity 94%.
Embodiment 5
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by 4-nitro-o-phenylenediamine (306mg, 2.0mmo1), 4- bromobenzaldehyde (555mg, 3.0mmo1) and L-carnitine
(48.4mg, 0.3mmol) is added to the in the mixed solvent of 8mL ethyl alcohol and 8mL water, and under electromagnetic agitation, 4h are reacted in 40 DEG C of heating, obtains
To crude product；
2) filtration of crude product for obtaining step 1), dries 2h at a temperature of 100 DEG C, obtains product 2- with ethyl alcohol recrystallization
(4- bromo phenyl) -5- nitro -1H- benzo [d] imidazoles, yield 97%, purity 98%.
Embodiment 6
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (324mg, 3.0mmo1), 3- nitrobenzaldehyde (151mg, 1.0mmo1) and L-carnitine
(48.4mg, 0.3mmol) is added in 30mL n-hexane, and under electromagnetic agitation, 3h is reacted in 25 DEG C of heating, obtains crude product；
2) filtration of crude product for obtaining step 1) dries 1h at a temperature of 120 DEG C, obtains product 2- (3- nitrobenzene
Base) -1H- benzo [d] imidazoles, yield 96%, purity 95%.
Embodiment 7
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (216mg, 2.0mmo1), Benzaldehyde,2-methoxy (136mg, 1.0mmo1) and L-carnitine
(16.1mg, 0.1mmol) is added in 1, the 2- dichloroethanes of 6mL, and under electromagnetic agitation, 1h is reacted in 50 DEG C of heating, is slightly produced
Object；
2) filtration of crude product for obtaining step 1) dries 5h at a temperature of 70 DEG C, obtains product 2- (2- methoxybenzene
Base) -1H- benzo [d] imidazoles, yield 95%, purity 92%.
Embodiment 8
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (108mg, 1.0mmo1), 2,4- dichlorobenzaldehyde (175mg, 1.0mmo1) and L-carnitine
(16.1mg, 0.1mmol) is added in 95% ethyl alcohol of 5mL, and under electromagnetic agitation, 3h is reacted in 60 DEG C of heating, obtains crude product；
2) filtration of crude product for obtaining step 1), dries 1h at a temperature of 90 DEG C, obtains product 2- with ethyl alcohol recrystallization
(2,4- dichloride base phenyl) -1H- benzo [d] imidazoles, yield 95%, purity 97%.
Comparative example 1
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (108mg, 1.0mmo1), 4-methoxybenzaldehyde (136mg, 1.0mmo1) and tannic acid
(48.8mg, 0.03mmol) is added in 95% ethyl alcohol of 5mL, and under electromagnetic agitation, 1h is reacted in 60 DEG C of heating；
2) mixture after heating reaction in step 1) is poured into water, obtains flocculent deposit, 2h is stood in refrigerator, takes
It filters out, dries, obtain product 2- (4- methoxyphenyl) -1H- benzo [d] imidazoles with ethyl alcohol recrystallization, yield 92% is pure
Degree is 90%.
Comparative example 2
A kind of synthetic method of benzimidazoles compound, reaction equation are as follows:
The following steps are included:
1) by o-phenylenediamine (108mg, 1.0mmo1), p-chlorobenzaldehyde (141mg, 1.0mmo1) and tannic acid (49.8mg,
It 0.03mmol) is added in 5mL hexamethylene, under electromagnetic agitation, 7h is reacted in 80 DEG C of heating；
2) mixture after heating reaction in step 1) is poured into water, obtains flocculent deposit, 2h is stood in refrigerator, takes
It filters out, dries, obtain product 2- (4- chloro phenyl) -1H- benzo [d] imidazoles, yield 35%, purity with ethyl alcohol recrystallization
It is 90%.
Claims (9)
1. a kind of synthetic method of benzimidazoles compound, which is characterized in that
The synthetic route of the synthetic method are as follows:
The synthetic method the following steps are included:
1) substituted o-phenylenediamine (I), aromatic aldehyde (II) and L-carnitine are added in solvent, carry out heating reaction, obtained thick
Product；
2) filtration of crude product for obtaining step 1), collects solid matter, and drying obtains benzimidazoles compound (III)；
The Ar of the aromatic aldehyde is o-, m- and/or aligns the phenyl ring for having substituent group, and the substituent group includes halogen, methoxy
Base and nitro；
The R of the substituted o-phenylenediamine includes hydrogen and nitro.
2. synthetic method according to claim 1, which is characterized in that the synthetic method after step 2), further include by
The step of benzimidazoles compound after drying is recrystallized.
3. synthetic method according to claim 1 or 2, which is characterized in that in step 1), substituted o-phenylenediamine and aromatic aldehyde
Molar ratio be 1-3:1-3.
4. synthetic method according to claim 1 or 2, which is characterized in that in step 1), substituted o-phenylenediamine and left-handed meat
The molar ratio of alkali is 1:0.05-0.15.
5. synthetic method according to claim 1 or 2, which is characterized in that in step 1), solvent is selected from n-hexane, hexamethylene
One of alkane, 1,2- dichloroethanes, ethyl alcohol, chloroform and water are a variety of.
6. synthetic method according to claim 5, which is characterized in that in step 1), solvent is 95% ethyl alcohol.
7. synthetic method according to claim 1 or 2, which is characterized in that in step 1), the molal quantity of substituted o-phenylenediamine
Volume ratio with solvent is 1mmol:3-10mL.
8. synthetic method according to claim 1 or 2, which is characterized in that in step 1), the temperature for heating reaction is 25-
80 DEG C, the time for heating reaction is 1-4h.
9. synthetic method according to claim 1 or 2, which is characterized in that in step 2), the temperature of drying is 60-120
DEG C, the time of drying is 1-5h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114591248A (en) * | 2022-04-24 | 2022-06-07 | 湖南工程学院 | Method for preparing benzimidazole compound by using carbazolyl conjugated microporous polymer photocatalysis |
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| CN103435551A (en) * | 2013-06-28 | 2013-12-11 | 浙江工业大学 | 2-substituted benzimidazole compound preparation method |
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| CN103435551A (en) * | 2013-06-28 | 2013-12-11 | 浙江工业大学 | 2-substituted benzimidazole compound preparation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114591248A (en) * | 2022-04-24 | 2022-06-07 | 湖南工程学院 | Method for preparing benzimidazole compound by using carbazolyl conjugated microporous polymer photocatalysis |
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