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2-chloro-10,11-Dihydro-11-oxodibenzo [b, f] [1, 4] thiazepine-11 (10-H)-one preparing method

A technology of thiazepines and chlorinated diphenyl sulfides, which is applied in the field of preparation of organic compounds, can solve the problems of environmental pollution, high cost, and low yield, and achieve reduced production costs, simple method, and high reaction yield Effect

Inactive Publication Date: 2014-01-22
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the above method can prepare 2-chloro-dibenzo[b,f][1,4]thiazepine-11-[10H]ketone; but there are various deficiencies, some yields are low, some cost High, some serious environmental pollution

Method used

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  • 2-chloro-10,11-Dihydro-11-oxodibenzo [b, f] [1, 4] thiazepine-11 (10-H)-one preparing method
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  • 2-chloro-10,11-Dihydro-11-oxodibenzo [b, f] [1, 4] thiazepine-11 (10-H)-one preparing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of 2-nitro-4'-chlorodiphenyl sulfide

[0031]

[0032] Put 47.5g of o-nitrochlorobenzene, 52g of p-chlorothiophenol, and 210g of alcohol into a 500ml reaction bottle, stir and heat to 60°C, then start to drop 44g of 30% liquid caustic soda for about 1 hour, and stir for 30 Minutes, start to heat up to 80°C, reflux for 2 hours, cool to 20°C with cooling water, and filter with suction to obtain 76g of nitro compounds with a purity of 99.5% and a yield of 95%.

Embodiment 2

[0033] Example 2 Preparation of 2-amino-4'-chlorodiphenylsulfide

[0034]

[0035] 75g of the nitro substance obtained in Example 1, 750ml of ethanol, 3.75g of 10% palladium charcoal are dropped into a 1L autoclave successively, replaced 3 times with nitrogen, stirred and heated up, at 70°C to 80°C, the pressure is under 2.0Mpa, Reciprocate hydrogenation until the reading of the hydrogen pressure gauge does not change anymore, keep it warm for 1 hour, cool to room temperature, release the pressure, discharge the material, and concentrate the filtrate to dryness to obtain 63.2g of thick material amino, with a purity of 99%, and a yield of 95%. .

Embodiment 3

[0036] Example 3 Preparation of 2-phenoxycarboxamido-4'-chloro-diphenylsulfide

[0037]

[0038] Put 60 g of the amino concentrated solution obtained in Example 2 into a 1000 ml reaction bottle, add 500 ml of toluene, 51 g of 30% liquid caustic soda, and slowly add 59.8 g of phenyl chloroformate dropwise at 50 ° C, and the dropwise addition is completed in about 3 hours. After completion, keep the reaction for 2 hours, then pour it into a separatory funnel, separate the alkali layer, wash with 2x100ml water, separate the water, and remove the toluene from the organic layer at 90°C / -0.095Mpa under reduced pressure to obtain a thick acylate Concentrate 81.5g, purity 98.5%, yield 89.98%.

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Abstract

The invention discloses a 2-chloro-10, 11-Dihydro-11-oxodibenzo [b, f] [1, 4] thiazepine-11 (10-H)-one preparing method. The method comprises the steps that o-nitro chloro benzene which is low in price and easy to get is used for condensation with 4-chlorothiophenol to obtain 2-nitro-4'-chlorodiphenyl sulfide, then reduction is carried out to obtain 2-amino-4'-chlorine-diphenyl sulfide; then acylation with chloroformate is carried out, and finally Friedel-Crafts reaction is carried out to obtain 2-chloro-10, 11-Dihydro-11-oxodibenzo [b, f] [1, 4] thiazepine-11 (10-H)-one. According to the preparing method, reaction conditions are mild, raw materials used for the reaction are wide in source, reaction yield is high, reproducibility is good, product quality is stable, the preparing process is simple, initial raw material o-nitro chloro benzene is large-tonnage products in China, the o-nitro chloro benzene is low in price and easy to get, production cost is greatly lowered, and industrial production is convenient.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of 2-chloro-dibenzo[b,f][1,4]thiazepine-11-[10H]one. Background technique [0002] Clothiapine has better anti-illusion, delusional and anti-excitatory agitation effects; it is used for the treatment of acute and chronic schizophrenia, and has a good effect on controlling agitation, hallucinations, and delusions, and is also used for the treatment of anxiety, drug dependence and alcoholism. [0003] 2-Chloro-dibenzo[b,f][1,4]thiazepin-11-[10H]one is a key intermediate in the synthesis of clothiapine. At present, there are three traditional methods for preparing 2-chloro-dibenzo[b,f][1,4]thiazepin-11-[10H]one: [0004] In 1965, J. Schmutz and others reported that 2-chloro-dibenzo[ b,f][1,4]thiazepin-11-[10H]one; in 1983, Zdeněk Polívka et al. 2-Chloro-dibenzo[b,f][1,4]thiazepine-11-[10H]one was prepared by intramolecular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D281/16
CPCC07D281/16
Inventor 沈建伟
Owner SUZHOU JINGYE MEDICINE & CHEM
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