Preparation method of 2-methylthio-5-benzothiazole

A technology of bromobenzothiazole and mercaptobenzothiazole, which is applied in the field of synthesis of organic compounds, can solve the problems of large discharge of three wastes, long synthesis route, and low reaction yield, and achieve less discharge of three wastes, reduced corrosion, and high reaction yield high effect
CN102010385AInactive Publication Date: 2011-04-13ZHEJIANG UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG UNIV
Publication Date
2011-04-13
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a preparation method of 2-methylthio-5-benzothiazole, successively comprising the following steps: 1) mixing ethanol, a sodium hydroxide solution, 2-mercaptobenzothiazole and bromoethane to react until the 2-mercaptobenzothiazole is completely reacted; 2) cooling the product obtained by step 1) to room temperature, splitting phases, washing, and carrying out reduced pressure distillation and the like to obtain 2-methylthio benzothiazole; 3) dissolving the 2-methylthio benzothiazole into low-grade halohydrocarbon, and adding N-bromosuccinimide to react; and 4) after the reactive fluid obtained in step 3) is cooled to room temperature, successively filtering, washing, drying and carrying out reduced pressure distillation to obtain the wax-state solid product of the salmon 2-methylthio-5-benzothiazole. The 2-methylthio-5-benzothiazole prepared according to the method disclosed in the invention has the characteristics of simple technology, high yield, low cost, small three-waste discharge and the like.
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Description

technical field

[0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 2-ethylthio-5-bromobenzothiazole (5-bromo-2-(ethylthio)benzo[d]thiazole). Background technique

[0002] 2-Ethylthio-5-bromobenzothiazole, which has the formula C 9 h 8 BrNS 2 , the structural formula is shown in formula 1; it is an important intermediate for the synthesis of a new type of cancer treatment drug enzyme kinase inhibitor IGF-1R, in the patent WO2007056170, the synthetic method used is based on 2-mercapto-5-bromobenzothiazole The target product is obtained by reacting the starting material with a halogenated hydrocarbon. According to the literature (W.A.Boggust and W.Cocker, Journal of the Chemical Society (Resumed) 1949, 355-362.), the method of introducing the bromine atom at the 5-position of the benzothiazole ring: through nitration and reduction to obtain 5-amino Benzothiazole, and then diazotization and Sandmeyer reacti...

Claims

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