Unlock instant, AI-driven research and patent intelligence for your innovation.

Benzimidazolyl substituted phenyl thiazolinone derivative and synthesis method thereof

A phenylthiazolinone and benzimidazole-based technology, which is applied in the field of benzimidazolyl-substituted phenylthiazolinone derivatives and their synthesis, achieves the effects of simple reaction operation, high reaction yield, and improved reaction speed

Inactive Publication Date: 2012-05-02
NANJING UNIV OF TECH
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few research reports on the benzimidazolyl-substituted phenylthiazolinone derivatives synthesized by the present invention, and the synthesis of benzimidazolyl-substituted phenylthiazolinone derivatives by microwave method has not been reported.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Benzimidazolyl substituted phenyl thiazolinone derivative and synthesis method thereof
  • Benzimidazolyl substituted phenyl thiazolinone derivative and synthesis method thereof
  • Benzimidazolyl substituted phenyl thiazolinone derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Synthesis of 3-benzimidazol-2-yl-2-chlorophenylthiazolin-4-one

[0019] In a 250ml three-neck flask, add 0.01mol of N-benzimidazolyl-2-chlorophenylimine, 0.01mol of thioglycolic acid, dissolve in 100ml of toluene, and heat to 105°C under 300W microwave irradiation, and react for 20min. After cooling, filter and wash with ethanol. Then recrystallize with ethanol to obtain the product, the product is light yellow solid, yield: 83%. Melting point: 219~220℃.

[0020]

[0021] 1 H NMR (DMSO-d6, 300MHz): 4.04, 4.13 (d, 2H, CH 2 ), 6.83(s, 1H, CH), 7.05-7.55(m, 8H, H ring ), 12.47(s, 1H, NH benzimidazole ).

[0022] IR (cm -1 ): 3063, 2918, 1684, 1536, 1470, 1111.

[0023] The bactericidal activity test shows that: when the concentration is 20ppm, the bactericidal rates of sulfate-reducing bacteria and iron bacteria reach 98.1% and 85.3% respectively in 1 hour.

Embodiment 2

[0025] Synthesis of 3-benzimidazol-2-yl-2-p-nitrophenylthiazolin-4-one

[0026] In a 250ml three-necked flask, add 0.01mol of N-benzimidazolyl-4-nitrophenylimine synthesis, 0.013mol of thioglycolic acid, dissolve in 100ml of ethanol, then add 0.3ml of glacial acetic acid, and irradiate the mixture under 100W microwave Under the light, it was heated to 105°C, reacted for 10 minutes, filtered after cooling, and washed with toluene. Then recrystallize with ethanol to obtain the product as a yellow solid, yield: 71%. Melting point: 225-226°C.

[0027]

[0028] 1 H NMR (DMSO-d6, 500MHz): 4.01, 4.23 (d, 2H, CH 2 ), 6.90(s, 1H, CH), 7.09-8.19(m, 8H, H ring ), 12.41(s, 1H, NH benzimidazole ).

[0029] IR (cm -1 ): 3077, 2927, 1710, 1604, 1534, 1486.

[0030] The bactericidal activity test shows that when the concentration is 20ppm, the bactericidal rates of sulfate-reducing bacteria and iron bacteria reach 97.5% and 85% respectively in 1 hour.

Embodiment 3

[0032] Synthesis of 3-benzimidazol-2-yl-2-p-methylphenylthiazolin-4-one

[0033] In a 250ml three-neck flask, add 0.01mol of N-benzimidazolyl-4-methylphenylimine, 0.011mol of thioglycolic acid, dissolve in 100ml of toluene, heat to 115°C under 400W microwave irradiation, and react for 15min , filtered after cooling, and washed with toluene. Then recrystallize with ethanol to obtain the product, the product is off-white solid, yield: 80%. Melting point: 255-256°C.

[0034]

[0035] 1 H NMR (DMSO-d6, 300MHz): 2.31(t, 3H, CH 3 ), 3.91, 4.14 (d, 2H, CH 2 ), 6.73(s, 1H, CH), 7.08-7.45(m, 8H, H ring ), 12.25(s, 1H, NH benzimidazole ).

[0036] IR (cm -1 ): 3051, 2919, 1703, 1536, 1484.

[0037] The bactericidal activity test shows that: when the concentration is 10ppm, the bactericidal rate of sulfate-reducing bacteria and iron bacteria reaches 95.6% and 84.7% respectively in 1 hour.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a benzimidazolyl substituted phenyl thiazolinone derivative and a synthesis method thereof. The series of the derivative is shown as a general formula I, wherein R is hydrogen, alkyl of C1 to C5, alkoxy of C1 to C5, halogen or nitryl. The synthesis method comprises the following steps of: dissolving N-benzimidazolyl substituted phenyl imine and mercaptoacetic acid in terms of molar ratio being 1: (1-1.5) by using an organic solvent; heating to 105 to 115 DEG C and reacting for 10 to 20 minutes under microwave radiation of between 100 and 400W; cooling, filtering, washing and recrystallizing; and thus obtaining the benzimidazolyl substituted phenyl thiazolinone derivative. The synthesis method has the advantages of short reaction time, high yield and easiness for industrialization.

Description

technical field [0001] The invention relates to a benzimidazole-substituted phenylthiazolinone derivative and a synthesis method thereof. Background technique [0002] Heterocyclic compounds are widely used in medicine, pesticides, dyes, materials and other fields, especially nitrogen-containing single heterocyclic compounds or condensed heterocyclic compounds with special structures have attracted more and more chemists due to their strong physiological activity. attention. [0003] Benzimidazole heterocyclic compounds have good biological activity, and the research on compounds constructed from benzimidazole heterocyclic rings has attracted widespread attention of medicinal chemists. A large number of studies have shown that benzimidazole compounds have anti-parasitic, anti-bacterial, anti-inflammatory, anti-cancer and other drug activities. Thiazolone heterocyclic compounds have a wide range of biological activities, and can be used as fungicides, insecticides, plant gr...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A01P1/00
Inventor 徐炎华胡俊于鹏周桃玉
Owner NANJING UNIV OF TECH