Benzimidazole Schiff base and synthesis method thereof

A technology of benzimidazole and aminobenzimidazole, which is applied in the field of microwave synthesis of benzimidazole Schiff base, achieves the effects of high reaction yield, high sterilization rate and simple reaction operation

Inactive Publication Date: 2014-06-25
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the introduction of imine active groups on the benzimidazole ring, and there is no report on the synthesis of benzimidazole imines by microwave method.

Method used

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  • Benzimidazole Schiff base and synthesis method thereof
  • Benzimidazole Schiff base and synthesis method thereof
  • Benzimidazole Schiff base and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of N-Benzimidazolyl-1-phenylimine

[0020] In a 250ml three-neck flask, add 0.01mol of 2-aminobenzimidazole, 0.01mol of benzaldehyde, and 100ml of toluene, then add 0.1ml of piperidine, heat to 105°C under 400W microwave irradiation, react for 20min, and filter after cooling , washed with ethanol. Then recrystallize with ethanol to obtain the product, the product is a yellow solid, the yield: 85%. Melting point: 160-161°C.

[0021]

[0022] 1 H NMR (DMSO-d6, 300MHz): 12.67(s, 1H, NH benzimidazole ), 9.46(s, 1H, H arom ), 6.85-8.07 (m, 9H, H ring ).

[0023] IR (cm -1 ): 3054, 2759, 1666, 1565, 1480.

[0024] The bactericidal activity test shows that: when the concentration is 20ppm, the bactericidal rate of sulfate-reducing bacteria and iron bacteria reaches 92.2% and 80.2% respectively in 1 hour.

Embodiment 2

[0026] Synthesis of N-benzimidazolyl-4-fluorophenylimine.

[0027] In a 250ml three-neck flask, add 0.01mol of 2-aminobenzimidazole, 0.01mol of p-fluorobenzaldehyde, and 100ml of ethanol, then add 0.3ml of glacial acetic acid, and heat to 105°C under 100W microwave irradiation, react for 20min, and cool Then filter and wash with toluene. Then recrystallize with ethanol to obtain the product, the product is a yellow solid, the yield: 80%. Melting point: 185-186°C.

[0028]

[0029] 1 H NMR (DMSO-d6, 300MHz): 12.65 (s, 1H, NH benzimidazole ), 9.46(s, 1H, H arom ), 7.07-8.17 (m, 7H, H ring ).

[0030] IR (cm -1 ): 3065, 2753, 1615, 1587, 1461.

[0031] The bactericidal activity test showed that: when the concentration was 20ppm, the bactericidal rates of sulfate-reducing bacteria and iron bacteria reached 96.7% and 85.1% respectively in 1 hour.

Embodiment 3

[0033] Synthesis of N-Benzimidazolyl-4-methylphenylimine

[0034] In a 250ml three-neck flask, add 0.01mol of 2-aminobenzimidazole, 0.01mol of p-fluorobenzaldehyde, and 100ml of toluene, then add 0.2ml of pyridine, and heat to 115°C under 400W microwave irradiation, react for 5min, and cool Filter and wash with toluene. Then recrystallize with ethanol to obtain the product, the product is a yellow solid, the yield: 72%. Melting point: 238-239°C.

[0035]

[0036] 1 H NMR (DMSO-d6, 300MHz): 12.65 (s, 1H, NH benzimidazole ), 9.40(s, 1H, H arom ), 7.07-7.97 (m, 8H, H ring ), 2.42 (s, 3H, CH 3 ).

[0037] IR (cm -1 ): 3054, 2757, 1666, 1566, 1440.

[0038] The bactericidal activity test shows that: when the concentration is 10ppm, the bactericidal rates of sulfate-reducing bacteria and iron bacteria reach 91.3% and 80% respectively in 1 hour.

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Abstract

The invention discloses a benzimidazole Schiff base and a synthesis method thereof. The structure formula of the compound is as follows: FORMULA, wherein R is hydrogen, C1-C5 alkyl, C1-C5 alkoxy, halogen or nitryl. The synthesis method comprises the following steps of: dissolving 2-aminobenzimidazole and substituted benzaldehyde in the molar ratio of 1: (1-1.5) by organic solvent; adding catalyst; heating to 105-115 degrees centigrade by 100-400W microwave irradiation; reacting for 5-20min; cooling; filtering; washing; and re-crystallizing to obtain series of derivatives of benzimidazole Schiff base. The invention has the advantages of short reaction time, high yield and easy industrialization.

Description

technical field [0001] The invention relates to a synthesis method of a benzimidazole Schiff base; in particular, it relates to a microwave synthesis method of a benzimidazole Schiff base. Background technique [0002] In recent years, heterocyclic chemistry has been a major component of organic chemistry. In today's organic compounds, the number of heterocyclic compounds accounts for about one-third of the total. Nitrogen-containing heterocyclic compounds are an important branch of heterocyclic compounds. As intermediates of pharmaceuticals, pesticides, dyes and other fine chemical products, nitrogen-containing heterocyclic compounds and their derivatives are more and more widely used. [0003] 2-aminobenzimidazole (2-AB for short) is a fine chemical raw material with wide application value. It has important applications in pesticides, medicine and other fields, and has good bactericidal activity. The imidazole ring and benzimidazole heterocycle have antiparasitic, antib...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/30A01P1/00A61P31/04
Inventor 万嵘徐炎华胡俊周桃玉于鹏
Owner NANJING TECH UNIV
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