CN103739554B - A kind of method preparing 2-alkyl benzimidazole compounds - Google Patents

A kind of method preparing 2-alkyl benzimidazole compounds Download PDF

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CN103739554B
CN103739554B CN201310751991.2A CN201310751991A CN103739554B CN 103739554 B CN103739554 B CN 103739554B CN 201310751991 A CN201310751991 A CN 201310751991A CN 103739554 B CN103739554 B CN 103739554B
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oxymethylene
benzimidazole compounds
raw material
alkyl benzimidazole
leave standstill
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CN103739554A (en
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刘玉婷
张晓莉
刘蓓蓓
靖春燕
王捷
梁钢涛
尹大伟
吕博
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Shaanxi University of Science and Technology
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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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen atoms

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  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a kind of method preparing 2-alkyl benzimidazole compounds, a is added in the reaction vessel of drying? mol O-Phenylene Diamine and b? mol aliphatic carboxylic acid, raw material mixed and leaves standstill, making it react, wherein a:b=1:(1 ~ 1.2); Make raw material continue reaction under again reaction vessel being placed in the temperature of 45 ~ 100 DEG C, obtain reaction mixture; Reaction mixture is cooled to room temperature, obtains suspension liquid, regulate its pH value to be 8 ~ 9, then washing, suction filtration, the filter cake obtained is thick product, by thick product recrystallization, obtains 2-alkyl benzimidazole compounds.The method experimental implementation is simple, desired raw material is cheap and easy to get, required experimental installation is simple, the reaction times is short, temperature of reaction is lower, aftertreatment is simple, the productive rate of target product is high, environmental protection, meeting industrial needs, is a kind of method of green syt 2-alkyl benzimidazole compounds of economical and convenient.

Description

A kind of method preparing 2-alkyl benzimidazole compounds
Technical field
The invention belongs to the field of chemical synthesis, particularly a kind of method preparing 2-alkyl benzimidazole compounds.
Background technology
Benzimidazoles compound is a kind of important agricultural chemicals and medicine intermediate, and have the features such as special structure, physiologically active and reactive behavior due to it, Application Areas is very extensive.About the synthesis of this compounds, the study on the synthesis of the benzimidizole derivatives of especially 2-position replacement is more and more subject to people's attention.The method of the existing 2-of preparation substituted benzimidazole is reacted in a solvent with O-Phenylene Diamine and carboxylic acid.This legal system, for 2-substituted benzimidazole, often needs comparatively exacting terms---strong acidic condition, higher temperature, long time etc.Advocate Green Chemistry today, how to make the further greenization of the synthesis of benzimidazoles compound, remain an important problem.
Summary of the invention
The invention provides a kind of method preparing 2-alkyl benzimidazole compounds, the method experimental implementation is simple, the reaction times is short, productive rate is high.
For achieving the above object, the technical solution used in the present invention comprises the following steps:
1) in the reaction vessel of drying, add amol O-Phenylene Diamine and bmol aliphatic carboxylic acid, then raw material mixed and leave standstill, raw material being reacted, wherein a:b=1:(1 ~ 1.2);
2) make raw material continue reaction under reaction vessel being placed in the temperature of 45 ~ 100 DEG C, obtain reaction mixture;
3) reaction mixture is cooled to room temperature, obtains suspension liquid, regulate the pH value of suspension liquid to be 8 ~ 9, then washed, suction filtration, the filter cake obtained is thick product, by thick product recrystallization, obtains 2-alkyl benzimidazole compounds.
The structural formula of described aliphatic carboxylic acid is: R-COOH,
Wherein R=H ,-CH 3,-C 2h 5, n-C 3h 7, n-C 7h 15, n-C 9h 19, n-C 10h 21, n-C 17h 35,-CH 2sH ,-CH 2nH 2,-CHCl 2,-CH (CH 3) 2,-CHClCH 3,-CHBrCH 3,-CH 2cH 2sH ,-CH 2cH 2cl ,-CHSHCH 3,-CH 2cH 2nH 2,-(CH 2) 2cH 2nH 2,-C (CH 3) 2c 2h 5,-C (C 2h 5) 3, benzene Oxymethylene, 4-chlorobenzene Oxymethylene, 2-chlorobenzene Oxymethylene, 2,4 dichloro benzene Oxymethylene, 3-chlorobenzene Oxymethylene, 4-fluorobenzene Oxymethylene, 4-bromobenzene Oxymethylene, 4-iodobenzene Oxymethylene, 4-anisole Oxymethylene, 2-oil of mirbane Oxymethylene, alpha-naphthoxy methylene radical or β-naphthalene Oxymethylene.
Described step 1) is carried out at the temperature of 20 ~ 25 DEG C.
Described reaction vessel is mortar, is mixed by raw material in described step 1) by grinding, in grinding and standing process, raw material is reacted.
Described grinding and standing concrete time are: first grind 2 ~ 6min, leave standstill 15 ~ 20min, then grind 5 ~ 10min, leave standstill 20 ~ 30min, finally grind 15 ~ 20min, leave standstill 30 ~ 40min.
Described step 2) at the temperature of 45 ~ 100 DEG C, make raw material continue reaction be specially: first at 45 ~ 55 DEG C, react 20 ~ 40min, then 70 ~ 80 DEG C are warming up to, at 70 ~ 80 DEG C, react 40 ~ 60min, be finally warming up to 90 ~ 100 DEG C, at 90 ~ 100 DEG C, react 90 ~ 100min.
Described step 2) carry out in an oven.
Regulate the pH value of suspension liquid by the NaOH solution that mass concentration is 3 ~ 5% in described step 3).
Recrystallization solvent in described step 3) is dehydrated alcohol or anhydrous methanol.
The structural formula of obtained 2-alkyl benzimidazole compounds is:
Wherein R=H ,-CH 3,-C 2h 5, n-C 3h 7, n-C 7h 15, n-C 9h 19, n-C 10h 21, n-C 17h 35,-CH 2sH ,-CH 2nH 2,-CHCl 2,-CH (CH 3) 2,-CHClCH 3,-CHBrCH 3,-CH 2cH 2sH ,-CH 2cH 2cl ,-CHSHCH 3,-CH 2cH 2nH 2,-(CH 2) 2cH 2nH 2,-C (CH 3) 2c 2h 5,-C (C 2h 5) 3, benzene Oxymethylene, 4-chlorobenzene Oxymethylene, 2-chlorobenzene Oxymethylene, 2,4 dichloro benzene Oxymethylene, 3-chlorobenzene Oxymethylene, 4-fluorobenzene Oxymethylene, 4-bromobenzene Oxymethylene, 4-iodobenzene Oxymethylene, 4-anisole Oxymethylene, 2-oil of mirbane Oxymethylene, alpha-naphthoxy methylene radical or β-naphthalene Oxymethylene.
Compared with prior art, the present invention has following beneficial effect:
The invention provides a kind of method preparing 2-alkyl benzimidazole compounds, with O-Phenylene Diamine and aliphatic carboxylic acid for raw material reaction generates 2-alkyl benzimidazole compounds, the method experimental implementation is simple, desired raw material is cheap and easy to get, required experimental installation is simple, the reaction times is short, temperature of reaction is lower, aftertreatment is simple, the productive rate of target product is high, environmental protection, meeting industrial needs, is a kind of method of green syt 2-alkyl benzimidazole compounds of economical and convenient.
Further, it is even and standing that mortar grinding put into by O-Phenylene Diamine and aliphatic carboxylic acid by the present invention, the heat produced in process of lapping can make raw material start to react, therefore grinding and leave standstill to hocket several times and be conducive to raw material and can react fully in the present invention, simple to operate.And after grinding evenly, mortar is put into baking oven, according to the particular case of this reaction, carry out stepped intensification heating, contribute to O-Phenylene Diamine and aliphatic carboxylic acid twice de-H in the reaction 2carrying out smoothly of O process.Namely at 45 ~ 55 DEG C, first react 20 ~ 40min can make first time de-H 2o process is carried out smoothly, at 70 ~ 80 DEG C, then reacts 40 ~ 60min can make the de-H of second time 2o process is carried out smoothly, at 90 ~ 100 DEG C, react 90 ~ 100min again can make product obtain drying to a certain extent, finally after adjust ph, utilize recrystallization to purify to product, make the productive rate of final 2-alkyl benzimidazole compounds can up to more than 90%.
Embodiment
Synthetic route of the present invention is:
Wherein R=H ,-CH 3,-C 2h 5, n-C 3h 7, n-C 7h 15, n-C 9h 19, n-C 10h 21, n-C 17h 35,-CH 2sH ,-CH 2nH 2,-CHCl 2,-CH (CH 3) 2,-CHClCH 3,-CHBrCH 3,-CH 2cH 2sH ,-CH 2cH 2cl ,-CHSHCH 3,-CH 2cH 2nH 2,-(CH 2) 2cH 2nH 2,-C (CH 3) 2c 2h 5,-C (C 2h 5) 3, benzene Oxymethylene, 4-chlorobenzene Oxymethylene, 2-chlorobenzene Oxymethylene, 2,4 dichloro benzene Oxymethylene, 3-chlorobenzene Oxymethylene, 4-fluorobenzene Oxymethylene, 4-bromobenzene Oxymethylene, 4-iodobenzene Oxymethylene, 4-anisole Oxymethylene, 2-oil of mirbane Oxymethylene, alpha-naphthoxy methylene radical or β-naphthalene Oxymethylene.
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1:
1) in the mortar of drying, add amol O-Phenylene Diamine and bmol formic acid (R=H), at 20 DEG C, first grind 5min, leave standstill 20min, then grind 10min, leave standstill 30min, finally grind 15min, leave standstill 40min, raw material is mixed, and raw material is reacted, wherein a:b=1:1;
2) mortar being placed in baking oven makes raw material continue reaction, first at 50 DEG C, reacts 30min, is then warming up to 80 DEG C, at 80 DEG C, reacts 60min, be finally warming up to 100 DEG C, react 90min, obtain reaction mixture at 100 DEG C;
3) reaction mixture is cooled to room temperature, obtain suspension liquid, the pH value of suspension liquid is regulated to be 8.5 by the NaOH solution that mass concentration is 5%, then (adding water directly to have adjusted in the suspension liquid after pH), suction filtration is washed, the filter cake obtained is thick product, by thick product dehydrated alcohol recrystallization, obtains benzoglyoxaline, its productive rate reaches more than 90%, and structural formula is:
M.p.(fusing point)=170 ~ 172 DEG C; IR(KBr, ν/cm -1): 3324.67,1588.31,1477.95,145.63,1409.68,1273.58,745.47.
Embodiment 2:
1) in the mortar of drying, amol O-Phenylene Diamine and bmol acetic acid (R=CH is added 3), at 25 DEG C, first grind 6min, leave standstill 15min, then grind 10min, leave standstill 28min, finally grind 18min, leave standstill 38min, raw material is mixed, and raw material is reacted, wherein a:b=1:1;
2) mortar being placed in baking oven makes raw material continue reaction, first at 48 DEG C, reacts 35min, is then warming up to 80 DEG C, at 80 DEG C, reacts 60min, be finally warming up to 100 DEG C, react 90min, obtain reaction mixture at 100 DEG C;
3) reaction mixture is cooled to room temperature, obtain suspension liquid, the pH value of suspension liquid is regulated to be 8 by the NaOH solution that mass concentration is 4%, then washed, suction filtration, the filter cake obtained is thick product, by thick product dehydrated alcohol recrystallization, obtains 2-tolimidazole, its productive rate reaches more than 90%, and structural formula is:
m.p.=179～181℃；IR（KBr，ν/cm -1）：3321.53,2998.24,1654.68,1589.45,1378.24。
Embodiment 3:
1) in the mortar of drying, amol O-Phenylene Diamine and bmol propionic acid (R=C is added 2h 5), at 22 DEG C, first grind 4min, leave standstill 18min, then grind 8min, leave standstill 26min, finally grind 20min, leave standstill 35min, raw material is mixed, and raw material is reacted, wherein a:b=1:1;
2) mortar being placed in baking oven makes raw material continue reaction, first at 52 DEG C, reacts 25min, is then warming up to 78 DEG C, at 78 DEG C, reacts 55min, be finally warming up to 98 DEG C, react 95min, obtain reaction mixture at 98 DEG C;
3) reaction mixture is cooled to room temperature, obtain suspension liquid, the pH value of suspension liquid is regulated to be 9 by the NaOH solution that mass concentration is 3%, then washed, suction filtration, the filter cake obtained is thick product, by thick product dehydrated alcohol recrystallization, obtains 2-ethyl benzo imidazole, its productive rate reaches more than 90%, and structural formula is:
m.p.=109～111℃；IR（KBr，ν/cm -1）：3302.71,1670.34,1590.25,3062.19,1452.61。
Embodiment 4
1) in the mortar of drying, amol O-Phenylene Diamine and bmol butanic acid (R=n-C is added 3h 7, i.e. n-propyl), at 23 DEG C, first grind 3min, leave standstill 17min, then grind 5min, leave standstill 23min, finally grind 16min, leave standstill 30min, raw material is mixed, and raw material is reacted, wherein a:b=1:1.1;
2) mortar being placed in baking oven makes raw material continue reaction, first at 45 DEG C, reacts 40min, is then warming up to 70 DEG C, at 70 DEG C, reacts 50min, be finally warming up to 95 DEG C, react 100min, obtain reaction mixture at 95 DEG C;
3) reaction mixture is cooled to room temperature, obtain suspension liquid, the pH value of suspension liquid is regulated to be 8.8 by the NaOH solution that mass concentration is 3.5%, then washed, suction filtration, the filter cake obtained is thick product, by thick product dehydrated alcohol recrystallization, obtains 2-propylbenzimidazole, its productive rate reaches more than 90%, and structural formula is:
Embodiment 5
1) in the mortar of drying, amol O-Phenylene Diamine and bmol n-caprylic acid (R=n-C is added 7h 15, i.e. n-heptyl), at 24 DEG C, first grind 2min, leave standstill 16min, then grind 6min, leave standstill 20min, finally grind 17min, leave standstill 33min, raw material is mixed, and raw material is reacted, wherein a:b=1:1.2;
2) mortar being placed in baking oven makes raw material continue reaction, first at 55 DEG C, reacts 20min, is then warming up to 75 DEG C, at 75 DEG C, reacts 40min, be finally warming up to 90 DEG C, react 98min, obtain reaction mixture at 90 DEG C;
3) reaction mixture is cooled to room temperature, obtain suspension liquid, the pH value of suspension liquid is regulated to be 8.2 by the NaOH solution that mass concentration is 4.5%, then washed, suction filtration, the filter cake obtained is thick product, by thick product dehydrated alcohol recrystallization, obtains 2-heptyl benzoglyoxaline, its productive rate reaches more than 90%, and structural formula is:
Embodiment 6 ~ 33 is identical with operating parameters with the step of embodiment, and the feedstock fat race carboxylic acid that it adds is specifically as shown in table 1 with the product 2-alkyl benzimidazole compounds obtained.
Table 1

Claims (5)

1. prepare a method for 2-alkyl benzimidazole compounds, it is characterized in that, comprise the following steps:
1) in the mortar of drying, add amol O-Phenylene Diamine and bmol aliphatic carboxylic acid, then by grinding raw material mixed and leave standstill, in grinding and standing process, raw material is reacted, wherein a:b=1:(1 ~ 1.2); Grinding and the concrete time left standstill are: first grind 2 ~ 6min, leave standstill 15 ~ 20min, then grind 5 ~ 10min, leave standstill 20 ~ 30min, finally grind 15 ~ 20min, leave standstill 30 ~ 40min; The structural formula of aliphatic carboxylic acid is: R-COOH, wherein R=H ,-CH 3,-C 2h 5, n-C 3h 7, n-C 7h 15, n-C 9h 19, n-C 10h 21, n-C 17h 35,-CH 2sH ,-CH 2nH 2,-CHCl 2,-CH (CH 3) 2,-CHClCH 3,-CHBrCH 3,-CH 2cH 2sH ,-CH 2cH 2cl ,-CHSHCH 3,-CH 2cH 2nH 2,-(CH 2) 2cH 2nH 2,-C (CH 3) 2c 2h 5,-C (C 2h 5) 3, benzene Oxymethylene, 4-chlorobenzene Oxymethylene, 2-chlorobenzene Oxymethylene, 2,4 dichloro benzene Oxymethylene, 3-chlorobenzene Oxymethylene, 4-fluorobenzene Oxymethylene, 4-bromobenzene Oxymethylene, 4-iodobenzene Oxymethylene, 4-anisole Oxymethylene, 2-oil of mirbane Oxymethylene, alpha-naphthoxy methylene radical or β-naphthalene Oxymethylene;
2) raw material is made to continue reaction under reaction vessel being placed in the temperature of 45 ~ 100 DEG C, be specially: first at 45 ~ 55 DEG C, react 20 ~ 40min, then 70 ~ 80 DEG C are warming up to, 40 ~ 60min is reacted at 70 ~ 80 DEG C, finally be warming up to 90 ~ 100 DEG C, at 90 ~ 100 DEG C, react 90 ~ 100min, obtain reaction mixture;
3) reaction mixture is cooled to room temperature, obtains suspension liquid, regulate the pH value of suspension liquid to be 8 ~ 9, then washed, suction filtration, the filter cake obtained is thick product, by thick product recrystallization, obtains 2-alkyl benzimidazole compounds.
2. the method preparing 2-alkyl benzimidazole compounds according to claim 1, is characterized in that: described step 1) be carry out at the temperature of 20 ~ 25 DEG C.
3. the method preparing 2-alkyl benzimidazole compounds according to claim 1, is characterized in that: described step 2) carry out in an oven.
4. the method preparing 2-alkyl benzimidazole compounds according to claim 1, is characterized in that: described step 3) middle mass concentration be 3 ~ 5% NaOH solution regulate the pH value of suspension liquid.
5. the method preparing 2-alkyl benzimidazole compounds according to claim 1, is characterized in that: described step 3) in recrystallization solvent be dehydrated alcohol or anhydrous methanol.
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