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Synthetic method of 2-mercaptobenzothiazole derivative

A synthesis method and derivative technology, applied in the direction of organic chemistry, etc., can solve problems such as high reaction temperature, complex production process, and difficult control of reaction conditions, and achieve the effects of mild reaction conditions, easy industrialization, and simple operation

Inactive Publication Date: 2013-02-06
INNER MONGOLIA UNIV OF TECH
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  • Description
  • Claims
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Problems solved by technology

[0003] There are many ways to synthesize 2-mercaptobenzothiazole. In the laboratory, it is mainly synthesized by reacting o-aminothiophenol or o-iodoaniline with carbon disulfide; in industry, o-nitrochlorobenzene method, aniline method, and mixing of nitrobenzene and aniline are mainly used. synthetic method, the production process of these synthetic methods is complex, the reaction conditions are difficult to control, the reaction temperature is high, the yield is low, the use of flammable and explosive carbon disulfide raw materials and the poor versatility of the synthetic method

Method used

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  • Synthetic method of 2-mercaptobenzothiazole derivative
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  • Synthetic method of 2-mercaptobenzothiazole derivative

Examples

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Embodiment 1

[0018] Embodiment 1, take o-iodoaniline as raw material synthesis 2-mercaptobenzothiazole (with anhydrous ferric chloride as catalyst)

[0019] Add 0.50mmol of o-iodoaniline, 1.50mmol of potassium ethyl xanthate, 0.05mmol of anhydrous ferric chloride and 0.025mmol of 1,1'-binaphthyl-2,2'- For bis-diphenylphosphine (L2), add 2 mL of N, N-dimethylformamide as a reaction solvent under an inert gas environment, and react at 110° C. for 6 hours. After cooling to room temperature, 3 mL of 3N hydrochloric acid was added to the reaction solution and stirred for 2 hours, then 10 mL of saturated sodium bicarbonate solution was added and stirred for 20 minutes. Then the reaction solution was extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, the organic components were collected, dried over anhydrous magnesium sulfate for 2 hours, after the desiccant was removed, the solvent was distilled off under reduced pressure t...

Embodiment 2

[0020] Embodiment 2, take o-iodoaniline as raw material to synthesize 2-mercaptobenzothiazole (with ferric chloride hexahydrate as catalyst)

[0021] Add 0.54mmol of o-iodoaniline, 1.62mmol of potassium ethyl xanthate, 0.054mmol of ferric chloride hexahydrate and 0.11mmol of 4,5-bisdiphenylphosphine-9,9 into a 50mL three-necked flask -Dimethylxanthene (L3), add 2 mL of N,N-dimethylformamide as a reaction solvent under an inert gas environment, and react at 110° C. for 6 hours. After cooling to room temperature, 3 mL of 3N hydrochloric acid was added to the reaction solution and stirred for 2 hours, then 10 mL of saturated sodium bicarbonate solution was added and stirred for 20 minutes. Then the reaction solution was extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, the organic components were collected, dried over anhydrous magnesium sulfate for 2 hours, after the desiccant was removed, the solvent was d...

Embodiment 3

[0022] Embodiment 3, take o-iodoaniline as raw material synthesis 2-mercaptobenzothiazole (with iron trifluoride as catalyst)

[0023] Add 0.55mmol of o-iodoaniline, 1.65mmol of potassium ethyl xanthate, 0.055mmol of ferric trifluoride and 0.11mmol of triphenylphosphine (L1) into a 50mL three-necked flask, and then Add 2 mL of N,N-dimethylformamide as a reaction solvent, and react at 110° C. for 6 hours. After cooling to room temperature, 3 mL of 3N hydrochloric acid was added to the reaction solution and stirred for 2 hours, then 10 mL of saturated sodium bicarbonate solution was added and stirred for 20 minutes. Then the reaction solution was extracted three times with ethyl acetate, the combined organic phases were washed with saturated sodium chloride solution, the organic components were collected, dried over anhydrous magnesium sulfate for 2 hours, after the desiccant was removed, the solvent was distilled off under reduced pressure to obtain crude product. The crude p...

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Abstract

The invention provides a method for synthesizing a 2-mercaptobenzothiazole derivative with 2-halogen phenylamine and alkyl xanthogenate as raw materials and relates to the technical fields of industry, agriculture and medicine. The synthetic method provided by the invention comprises that the 2-halogen phenylamine and alkyl xanthogenate are dissolved into an appropriate solvent, a ferric salt catalyst and a phosphine ligand are added, and a reaction is carried out for 2-6 hours under the condition that the temperature is 90-110 DEG C, thus the finished product is obtained. According to the synthetic method provided by the invention, the 2-halogen phenylamine and alkyl xanthogenate are taken as raw materials, no-toxic and available iron salt is taken as a catalyst, and the 2-mercaptobenzothiazole derivative can be rapidly and efficiently synthesized under the action of the phosphine ligand. The synthetic method provided by the invention has the advantages that adoption of an inflammable and explosive carbon disulfide raw material is avoided, reaction conditions are mild, operation is easy and simple, yield is high and industrialization is easy to realize.

Description

technical field [0001] The invention relates to the technical fields of industry, agriculture and medicine, in particular to a method for synthesizing 2-mercapto-substituted benzothiazole derivatives. Background technique [0002] 2-Mercaptobenzothiazole derivatives are important components of benzothiazole compounds and have wide application value in the fields of industry, agriculture and medicine. In industry, 2-mercaptobenzothiazole is a general-purpose rubber vulcanization accelerator, which has the characteristics of fast vulcanization acceleration, good vulcanization flatness, and no early vulcanization during mixing. It is also used in various rubbers such as sulfenic acid amines The main production raw material of vulcanization accelerator is widely used in rubber processing industry. 2-Mercaptobenzothiazole is also an important auxiliary agent and intermediate, and the 2-mercaptobenzothiazole derivatives obtained by combining it with an oil-soluble group have good...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/72
Inventor 竺宁索全伶高敏韩利民洪海龙杜玉英解瑞俊
Owner INNER MONGOLIA UNIV OF TECH
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