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2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile and preparation method thereof

A technology of benzotriazole base and benzotriazole, which is applied in the field of preparation of 2-methylene) malononitrile, can solve the problems such as no reference to literature reports, and achieve simple and easy reaction operation and low production cost. The effect of low, mild reaction conditions

Active Publication Date: 2019-01-18
TIANJIN NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, we have not checked the bibliographical reports about 2-((benzotriazolyl)(3-bromophenyl)methylene)malononitrile synthesis method

Method used

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  • 2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile and preparation method thereof
  • 2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile and preparation method thereof
  • 2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add benzotriazole (59.5 mg, 0.5 mmol), benzallyl dinitrile (77.1 mg, 0.5 mmol) and NBS (8.9 mg, 0.05 mmol) into a 50 mL single-necked round bottom flask equipped with a magnet, and Potassium sulfate (1.01g, 3.75 mmol) was reacted at 90°C for 120 minutes under stirring and temperature control, during which the reaction progress was monitored by TLC, and petroleum ether-ethyl acetate (v / v=5:1) was used as a developing solvent. Until the raw material is no longer consumed. After the reaction, add 20 mL of dichloromethane, stir well and then filter, wherein the oxidant potassium persulfate can be recovered. The organic phase in the above filtrate was collected, and the crude product of a was obtained after rotary evaporation. The crude product can be purified with petroleum ether-ethyl acetate (v / v=5:1) as eluent, and then purified by flash chromatography to obtain the pure product of a.

[0030] Compound a : m.p. 157-159 o c. 1 H NMR (CDCl 3 , 300 MHz): 8.19 (d, J=8.1...

Embodiment 2

[0032] Add benzotriazole (59.5 mg, 0.5 mmol) and 2-(4-methylbenzylidene)-malononitrile (84.0 mg, 0.5 mmol) respectively into a 50 mL single-necked round bottom flask equipped with a magnet, NBS (8.9 mg, 0.05 mmol), potassium persulfate (1.01 g, 3.75 mmol), started stirring and controlled the temperature at 90°C for 210 minutes, during which the reaction progress was monitored by TLC, and petroleum ether-ethyl acetate (v / v =5:1) as a developing agent. Until the raw material is no longer consumed. After the reaction, add 20 mL of dichloromethane, stir well and then filter, wherein the oxidant potassium persulfate can be recovered. The organic phase in the above filtrate was collected, and the crude product of b was obtained after rotary evaporation. The crude product can be further purified with petroleum ether-ethyl acetate (v / v=5:1) as eluent, and passed through a flash chromatography column to obtain the pure product of b.

[0033] Compound b : m.p. >200 o c. 1H NMR (CDC...

Embodiment 3

[0035] Add benzotriazole (59.5 mg, 0.5 mmol), 2-(4-bromobenzylidene)-malononitrile (115.98 mg, 0.5 mmol), NBS (8.9 mg, 0.05 mmol), potassium persulfate (1.01 g, 3.75 mmol), started stirring and controlled the temperature at 90°C for 210 minutes, during which the reaction progress was monitored by TLC, and petroleum ether-ethyl acetate (v / v= 5:1) as a developing agent. Until the raw material is no longer consumed. After the reaction, add 20 mL of dichloromethane, stir well and then filter, wherein the oxidant potassium persulfate can be recovered. The organic phase in the above filtrate was collected, and the crude product of c was obtained after rotary evaporation. The crude product can be purified with petroleum ether-ethyl acetate (v / v=5:1) as eluent, and then purified by flash chromatography to obtain the pure product of c.

[0036] Compound c : m.p. >200 o c. 1 H NMR (CDCl 3 , 300 MHz): δ 1 H NMR (CDCl 3 , 300MHz) 8.20-8.17 (m, 1H), 7.76-7.71 (m, 2H), 7.50-7.39 (m,...

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Abstract

The invention discloses a benzotriazolyl derivative corrosion inhibitor 2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile and a preparation method thereof. By adopting a one-pot method, raw materials benzotriazole, (3-bromobenzal)-malononitrile, N-bromo succinimide and potassium perosulfate react to prepare the 2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile. The technical operation is simple, the production cost is low, the environmental pollution is small, and the large-scale industrialized generation can be realized; and moreover, a product has the performance of inhibiting the corrosion for color metals; The 2-((benzotriazolyl) (3-bromophenyl)methylene)malononitrile has the advantages of low production cost and high profit margin, and is suitable for the industrialized mass production.

Description

[0001] This invention is funded by Tianjin Normal University Development Fund (043135202-XK1701). technical field [0002] The invention belongs to the technical field of organic synthesis and relates to a preparation method of 2-((benzotriazolyl)(3-bromophenyl)methylene)malononitrile. Background technique [0003] Benzotriazole is mainly used as water treatment agent, metal rust inhibitor and corrosion inhibitor. Widely used in circulating water treatment agent, antirust oil and grease products, also used in vapor phase corrosion inhibitor of copper and copper alloy, lubricating oil additive. In electroplating, it is used to purify silver, copper and zinc on the surface, and has anti-tarnish effect. BTA forms covalent bonds and coordination bonds with copper atoms, alternates with each other to form a chain polymer, and forms a multi-layer protective film on the surface of copper, so that the surface of copper does not undergo oxidation-reduction reactions, does not genera...

Claims

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Application Information

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IPC IPC(8): C07D249/18
CPCC07D249/18
Inventor 刘巨艳房智兴符强马建心原楚妍
Owner TIANJIN NORMAL UNIVERSITY
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