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Synthesis method of 10-oxa-10,11-dihydro-5H-dibenzo(b,f) azepine

A synthesis method and azapine technology, which is applied in the field of synthesis of 10-oxa-10,11-dihydro-5H-dibenzo[b,f]azepine, can solve the problem that NBS is expensive and unfavorable to the industry Eliminate problems such as chemical production and cumbersome treatment process, and achieve the effects of less catalyst consumption, short reaction steps and advanced process routes

Active Publication Date: 2010-07-21
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem with this process is that NBS is expensive and the processing process is cumbersome
This reaction mainly has the problem of low yield, which is unfavorable for industrial production

Method used

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  • Synthesis method of 10-oxa-10,11-dihydro-5H-dibenzo(b,f) azepine
  • Synthesis method of 10-oxa-10,11-dihydro-5H-dibenzo(b,f) azepine
  • Synthesis method of 10-oxa-10,11-dihydro-5H-dibenzo(b,f) azepine

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Experimental program
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Effect test

Embodiment 1

[0018] To 125g (effective ClO - Content is 66%) in calcium hypochlorite, add iminodibenzyl 39g (0.2mol), nitroxide free radical 4-hydroxyl-2,2,6,6-tetramethylpiperidine oxide (4-hydroxyl-TEMPO ) 0.36g, copper acetate 0.14g, sodium bicarbonate 134g, stir well, and react at 55°C for 7 hours. After the reaction, extract with (500ml) dichloromethane, wash the organic phase with 100ml of water, evaporate the solvent to dryness under reduced pressure to obtain the crude product, recrystallize the crude product with ethanol to obtain 36.3g of the product, the yield is 86.8%, and the melting point is 138°C .

Embodiment 2

[0020] To 125g (effective ClO - Add 39 g (0.2 mol) of iminodibenzyl (0.2 mol), 0.31 g of nitroxide radical TEMPO, 0.14 g of copper acetate, and 134 g of sodium bicarbonate into calcium hypochlorite (66%), stir evenly, and react at 55° C. for 7 hours. After the reaction, extract with 500ml of dichloromethane, wash the organic phase with 100ml of water, evaporate the solvent to dryness under reduced pressure to obtain the crude product, recrystallize the crude product with ethanol to obtain 35.5g of the product, the yield is 84.9%, and the melting point is 139°C.

Embodiment 3

[0022] To 125g (effective ClO - Content is 66%) in calcium hypochlorite, add iminodibenzyl 39g (0.2mol), nitroxide free radical 4-ethoxy-TEMPO 0.42g, copper acetate 0.14g, sodium bicarbonate 134g, stir well, at 55 °C for 7 hours. After the reaction, extract with 500ml of dichloromethane, wash the organic phase with 100ml of water, evaporate the solvent to dryness under reduced pressure to obtain the crude product, recrystallize the crude product with ethanol to obtain 37.1g of the product, the yield is 88.7%, and the melting point is 138°C.

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Abstract

The invention relates to a synthesis method of 10-oxa-10,11-dihydro-5H-dibenzo(b,f) azepine shown in the formula (I). The synthesis method comprises the following steps of: carrying out oxidizing reaction at 0-200 DEG C by taking 10,11-dihydro-5H-dibenzo(b,f) azepine shown in the formula (II) as a raw material, nitroxides shown in the formula (III) as a catalyst, acetate as a catalyst promoter, calcium hypochlorite as an oxidant and inorganic salt as a carrier, and after reaction, processing reaction liquid to obtain the 10-oxa-10,11-dihydro-5H-dibenzo(b,f) azepine shown in the formula (I). The invention has the advantages of short reaction step, high conversion rate and yield, advanced process path, mild reaction conditions, small catalyst consumption, no use of brom-containing reagent like NBS (N-bromosuccinimide), liquid bromine and the like, simple after-treatment and less pollution to the environment.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 10-oxa-10,11-dihydro-5H-dibenzo[b,f]azepine. (2) Background technology [0002] At present, the chemical synthesis methods of 10-oxa-10,11-dihydro-5H-dibenzo[b, f]azepine mainly include: 1. Using 10,11-dihydro-5H-dibenzo [b, f] Azepine is used as a raw material, hydrolyzed after bromination reaction with NBS (N-bromosuccinimide), and then oxidized with sodium hypochlorite (US6384217). The problem with this process is that NBS is expensive and the treatment process is cumbersome. 2. Using 10,11-dihydro-5H-dibenzo[b,f]azepine as raw material, under the catalysis of NHPI (N-hydroxyphthalimide) and benzaldehyde, and oxygen Oxidation reactions (Eur. J. Org. Chem. 2003, 3, 578). This reaction mainly has the problem of low yield, which is unfavorable for industrial production. Therefore, it is urgent to find a synthetic method with cheap and easy-to-obtain reaction materials, simple and quick ope...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/22
Inventor 苏为科金灿张丽车大庆蒋祖林
Owner ZHEJIANG UNIV OF TECH
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