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A kind of synthetic method of substituting o-phenylenediamine

A synthesis method and technology of o-phenylenediamine, applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxyl compounds, etc., can solve problems such as cumbersome synthesis steps

Active Publication Date: 2021-07-06
山东凯瑞化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, no matter what kind of synthesis of o-phenylenediamine, when preparing substituted o-phenylenediamine, the synthesis of o-phenylenediamine cannot be avoided, and the synthesis steps are cumbersome

Method used

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  • A kind of synthetic method of substituting o-phenylenediamine
  • A kind of synthetic method of substituting o-phenylenediamine
  • A kind of synthetic method of substituting o-phenylenediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] Add (E)-N'-(2-fluoro-6-nitrophenyl)-N,N-dimethylformamidine (2mmol, 422mg), DMSO (12mL), 2- Amino ethanol (10mmol, 610mg) and a magnetic stirring bar, the reaction tube was capped and placed in an oil bath with magnetic stirring and heated to 180°C for 1 hour. TLC analysis showed that the starting material (E)-N'-(2-fluoro-6-nitrophenyl)-N,N-dimethylformamidine disappeared and new spots appeared. LC-MS analysis confirmed the formation of the target product. After the reaction solution was cooled to room temperature, it was poured into a 250 mL round bottom flask filled with water (50 mL) and stirred for 10 minutes. The mixture was then transferred to a separatory funnel and extracted with ethyl acetate (4 x 50 mL). After combining the organic phases, they were washed with water (60 mL) and dried over anhydrous sodium sulfate for 6 hours. Viscous light yellow liquid was obtained after rotary evaporation. Silica gel column chromatography (mobile phase: eth...

Embodiment 2

[0050]

[0051] Add (E)-N'-(2-fluoro-6-nitrophenyl)-N,N-dimethylformamidine (6mmol, 1.266g), DMSO (25mL) into a 50mL single-necked round bottom flask, 2-Aminoethanol (30mmol, 1.83g) and a magnetic stir bar, the reaction bottle was placed in an oil bath with magnetic stirring and heated to reflux (189°C) for 2 hours. TLC analysis showed that the starting material (E)-N'-(2-fluoro-6-nitrophenyl)-N,N-dimethylformamidine disappeared and new spots appeared. LC-MS analysis confirmed the formation of the target product. After the reaction solution was cooled to room temperature, it was poured into a 500 mL round bottom flask filled with water (150 mL) and stirred for 10 minutes. The mixture was then transferred to a separatory funnel and extracted with ethyl acetate (3 x 160 mL). After combining the organic phases, they were washed with water (200 mL) and dried overnight over anhydrous sodium sulfate. Viscous light yellow liquid was obtained after rotary evaporation. Silica ge...

Embodiment 3

[0053]

[0054] Add (E)-N'-(2-fluoro-4-nitrophenyl)-N,N-dimethylformamidine (2mmol, 0.422g), DMSO (12mL), 2 -(Pyrrolidin-1-yl)ethylamine (10mmol, 1.14g) and a magnetic stirrer, the reaction tube was covered and heated to 180°C in an oil bath with magnetic stirring for 1 hour. TLC analysis showed that the raw material (E)-N'-(2-fluoro-4-nitrophenyl)-N,N-dimethylformamidine still existed, and after heating for another 30 minutes, TLC analysis showed that the raw material disappeared. LC-MS analysis confirmed the formation of the target product. After the reaction solution was cooled to room temperature, it was poured into a 250 mL round bottom flask filled with water (50 mL) and stirred for 10 minutes. The mixture was then transferred to a separatory funnel and extracted with ethyl acetate (3 x 50 mL). After combining the organic phases, they were washed with water (50 mL) and dried over anhydrous sodium sulfate for 6 hours. Viscous light yellow liquid was obtained after r...

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Abstract

The invention discloses a synthesis method of substituted o-phenylenediamine, which comprises heating N'-(2-fluorophenyl)-N,N-dimethylformamidine derivatives and alkylamine derivatives to 180-220°C The reaction can be obtained; the reaction process is as follows: where, R 1 is chlorine, bromine, nitro, methoxycarbonyl, cyano or acetyl, R 2 is hydrogen, fluorine, bromine, R 3 It is 2-hydroxyethyl, 2-methoxyethyl, (tetrahydrofuran-2-yl) methyl, 2-(pyrrolidin-1-yl) ethyl.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of substituted o-phenylenediamine. Background technique [0002] O-phenylenediamine is an important chemical intermediate, mainly used in the synthesis of pesticides, dyes, auxiliaries, photosensitive materials, etc., and has a wide range of uses and broad market prospects. Since the substitution of o-phenylenediamine can synthesize antipsychotic drugs, the pharmaceutical industry will be the field with the most potential for development of o-phenylenediamine. Substituted o-phenylenediamine is obtained by substitution reaction of o-phenylenediamine. At present, there are only three synthetic routes that are industrialized or have industrialization prospects, namely, the ammoniation of o-nitrochlorophenyl sulfide reduction method, the amination method of o-dichlorophenyl, and the catalytic hydrogenation reduction method of the amination of o-nitrochlorophenyl. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/08C07C215/16C07D295/13
CPCC07C213/08C07D295/13C07C215/16
Inventor 刘雪静韩迎闫鹏曹晗别福生
Owner 山东凯瑞化学有限公司