A kind of preparation method of 2-trifluoromethyl-9-allyl-9-thioxanthol

A technology of trifluoromethyl and thioxanthol, applied in the field of preparation of 2-trifluoromethyl-9-allyl-9-thioxanthol, which can solve environmental pollution, long reaction time, increased production costs, etc. problems, achieve the effects of reducing production costs, avoiding the use of reaction solvents, and reducing emissions

Active Publication Date: 2020-11-03
JIANGSU TOHOPE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the generation of the organometallic intermediate and the nucleophilic addition to the carbonyl of 2-trifluoromethyl-9-thioxanthone (II) are all completed in one step in the same system in this method, the operation steps are greatly simplified, but the reaction It takes a long time, and a large amount of organic solvent N,N-dimethylformamide (DMF) is used in the reaction process, and a large amount of organic waste liquid is generated during the preparation process. Due to the high boiling point of DMF and its miscibility with water, it is difficult to completely remove and recycle. Reuse, which not only easily causes environmental pollution but also increases production costs, does not meet the requirements of green production

Method used

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  • A kind of preparation method of 2-trifluoromethyl-9-allyl-9-thioxanthol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add tin powder (17.81g, 0.15mol) to a 500mL reaction bottle, and add 2-trifluoromethyl-9-thioxanthone (28.03g, 0.10mol) dropwise while stirring at room temperature (25°C). ) and allyl bromide (18.15g, 0.15mol).

[0026] After the dropwise addition, keep stirring at room temperature (25°C) for 1-2 hours. After the reaction, slowly add the reaction mixture dropwise into a 1L reaction flask containing 280.0g of saturated ammonium chloride solution and 225g of ethyl acetate. After dripping, keep stirring for 30 minutes, let stand to separate the liquid, collect the organic layer, remove the solvent from the organic layer under reduced pressure, and obtain 30.9 g of light brown oily liquid 2-trifluoromethyl-9-allyl-9-thioxanthol , yield 95.8%, purity (HPLC area normalization method) 90.0%.

Embodiment 2

[0028] Add tin powder (15.43g, 0.13mol) to a 500mL reaction bottle, and add 2-trifluoromethyl-9-thioxanthone (28.03g, 0.10mol) dropwise while stirring at room temperature (25°C). ) and allyl bromide (18.15g, 0.15mol).

[0029] After the dropwise addition, keep stirring at room temperature (25°C) for 1-2 hours. After the reaction, slowly add the reaction mixture dropwise into a 1L reaction flask containing 250.0g of saturated ammonium chloride solution and 200g of ethyl acetate. After dripping, keep stirring for 30 minutes, let stand to separate the liquid, collect the organic layer, remove the solvent from the organic layer under reduced pressure, and obtain 30.7 g of light brown oily liquid 2-trifluoromethyl-9-allyl-9-thioxanthol , yield 95.2%, purity (HPLC area normalization method) 98.6%.

Embodiment 3

[0031] Add tin powder (17.81g, 0.15mol) to a 500mL reaction bottle, and add 2-trifluoromethyl-9-thioxanthone (28.03g, 0.10mol) dropwise while stirring at room temperature (25°C). ) and allyl bromide (12.10g, 0.10mol) mixture.

[0032] After the dropwise addition, keep stirring at room temperature (25°C) for 1-2 hours. After the reaction, slowly add the reaction mixture dropwise into a 1L reaction flask containing 250.0g of saturated ammonium chloride solution and 200g of ethyl acetate. After dropping, keep stirring for 30 minutes, let stand to separate the liquid, collect the organic layer, remove the solvent from the organic layer under reduced pressure, and obtain 29.3 g of light brown oily liquid 2-trifluoromethyl-9-allyl-9-thioxanthol , yield 90.8%, purity (HPLC area normalization method) 96.5%.

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Abstract

The invention discloses a 2-trifluoromethyl-9-allyl-9-thiaxanthenol preparation method. The method takes 2-trifluoromethyl-9-thiaxanthenone (II) as a starting raw material, and in the presence of a catalyst and without participation of solvents, the 2-trifluoromethyl-9-thiaxanthenone (II) directly reacts with allyl bromide (III) to synthesize a targeted intermediate 2-trifluoromethyl-9-allyl-9-thiaxanthenol (I). The method provided by the invention is short in reaction time, high in yield, and simple in operation. The catalyst tin powder used in the method is cheap and easily available, so that production cost is reduced greatly. The method avoids the use of reaction solvents, decreases the three-waste (waste gas, waste water and industrial residue) emission, and meets basic requirements of green chemistry.

Description

technical field [0001] The invention relates to the field of chemical synthesis, and more specifically relates to a preparation method of 2-trifluoromethyl-9-allyl-9-thioxanthol. Background technique [0002] Flupenthixol hydrochloride, CAS registration number: 2413-38-9, chemical name: 2-trifluoromethyl-9-[3-[4-(β-hydroxyethyl)-1-piperazinyl]propylene Base] thioxanthene dihydrochloride, the chemical structure is as follows: [0003] . [0004] The commercially available compound preparation named "Deanxit" is a neuroleptic drug, and its main components are flupenthixol hydrochloride and melitracen. It is relatively popular in the domestic market, with a considerable share. [0005] The synthetic route disclosed in Chinese patent CN102786511B is shown in the following formula: [0006] . [0007] The route takes 2-trifluoromethyl-9-thioxanthone (II) as the starting material, and reacts with allyl bromide (III) in an organic solvent under the action of metal zinc or m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D335/16
CPCC07D335/16
Inventor 陆惠刚龚利锋顾晔周小军邹振荣
Owner JIANGSU TOHOPE PHARMA
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