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Preparation method of 11-aminodibenzo[b,f][1,4]thiazepine

A technology of aminodibenzo and thiazepine, which is applied in the direction of organic chemistry, can solve the problems of unfriendly environment and excess, and achieve the effect of being friendly to the environment, reducing side reactions, and simple operation

Inactive Publication Date: 2013-09-18
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the first step of the method, the chlorination yield is about 50%, and phosphorus oxychloride is used, and the excess is large, and industrial production will generate a large amount of phosphorus-containing wastewater, which is not friendly to the environment

Method used

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  • Preparation method of 11-aminodibenzo[b,f][1,4]thiazepine
  • Preparation method of 11-aminodibenzo[b,f][1,4]thiazepine

Examples

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Effect test

Embodiment 1

[0025] (1) Preparation of 2-amino-2'-cyanodiphenyl sulfide:

[0026] At room temperature, first add 50ml of DMF and 12ml of benzene to a 250ml three-neck flask with a dehydrator and a spherical condenser, add 11.2g of potassium carbonate and 8.6ml (10g) of o-aminothiophenol under mechanical stirring, and heat up and reflux for 1 hour (The temperature is 98°C). Dissolve 11.2 g of o-chlorobenzonitrile in 12 ml of DMF and add dropwise for 2 hours. After the dropwise addition is completed, the reaction temperature rises to 107° C., and the reaction is kept for 5 hours. After the reaction is completed, about 0.3 ml of water is dehydrated. Cool and filter to remove inorganic salts, decompress and distill to recover the solvent, slowly add it to 150ml of saturated brine, stir vigorously for half an hour, filter, and dry to obtain 18g of crude product, then recrystallize with ethyl acetate / petroleum ether mixed solvent to obtain nearly 16.4 g of white solid 2-amino-2′-cyanodiphenyl s...

Embodiment 2

[0038] (1) Preparation of 2-amino-2'-cyanodiphenyl sulfide:

[0039] At room temperature, first add 100ml of DMF and 24ml of benzene to a 250ml three-neck flask with a dehydrator and a spherical condenser, add 22.4g of potassium carbonate and 17.2ml (20g) of o-aminothiophenol under mechanical stirring, and heat up and reflux for 1 hour After (the temperature is 98°C). Dissolve 11.5 g of o-chlorobenzonitrile in 25 ml of DMF and add dropwise for 2 hours. After the dropwise addition is complete, the reaction temperature rises to 108° C., and the reaction is kept for 5 hours. After the reaction is completed, a total of about 0.5 ml of dehydration is completed. Cool and filter to remove inorganic salts, decompress and distill to recover the solvent, slowly add it to 150ml of saturated brine, stir vigorously for half an hour, filter, and dry to obtain 18g of crude product, then recrystallize with ethyl acetate / petroleum ether mixed solvent to obtain nearly 32.2 g of white solid 2-a...

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Abstract

The invention discloses a preparation method of 11-aminodibenzo[b,f][1,4]thiazepine. The method comprises the following steps: reacting 2-aminobenzenethiol with 2-chlorobenzonitrile in a mixed solvent of N,N-dimethyl formamide and benzene to prepare 2-amino-2'-nitrilediphenyl sulfide, and reacting 2-amino-2'-nitrilediphenyl sulfide with sodium tert-butoxide or potassium tert-butoxide, and carrying out ring closure to prepare the target product 11-aminodibenzo[b,f][1,4]thiazepine. The method has the advantages of simple and safe operation, less byproducts, environmental protection and the like.

Description

technical field [0001] The invention relates to the synthesis of chemical substances, in particular to a preparation method of 11-aminodibenzo[b,f][1,4]thiazepine. Background technique [0002] 11-Aminodibenzo[b,f][1,4]thiazepine is an intermediate for the preparation of quetiapine, and quetiapine hemifumarate is one of the important drugs for the treatment of schizophrenia at home and abroad , Therefore, the synthesis of its intermediate 11-aminodibenzo[b,f][1,4]thiazepine is of great significance. [0003] 11-Aminodibenzo[b,f][1,4]thiazepine, the structural formula is , molecular formula: C 13 h 10 N 2 S, the molecular weight is 226. [0004] Existing methods for synthesizing 11-aminodibenzo[b,f][1,4]thiazepines include: [0005] As disclosed in the literature (Synthesis of 11-Aminodibenzo[b,f][1,4]thiazepinesandFluoroDerivatives, J.HeterocyclicChem., 34,465,1997) and the literature A Process for the preparation of Quetiapine (WO2009095529), the reaction of o-aminot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D281/16
Inventor 赵志伟洪镛裕刘艳陈娟孙学佳
Owner EAST CHINA NORMAL UNIV
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