Catalyst-free technique for synthesizing phenothiazine drug intermediate

A technology of phenothiazines and intermediates, which is applied in the field of drug synthesis, can solve problems such as the complex structure of aniline, and achieve the effects of cheap and easy-to-obtain raw materials, high yield, and easy operation

Active Publication Date: 2016-06-15
BEIJING FANBO BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In 2011, Tao et al. used ligand-free CuI to catalyze 2-bromo-N-(2-iodophenyl)aniline and thioacetamide in a reactor Two consecutive C-S couplings give phenothiazines (Synlett, 2011, (1), 134-138); however, its starting material 2-bromo-N-(2-iodophenyl) Aniline has a complex structure and requires multi-step synthesis to obtain

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Take a dry ground test tube with a magnetic stirring bar, add 2mmol cesium carbonate, 0.5mmol S-2-acetamidophenyl thioacetate, o-bromoiodobenzene, 2mL of N,N-dimethylformamide, and use The rubber anti-port plug is fastened and sealed, vacuumed with an oil pump on the Schlenk vacuum line, and then filled with argon for replacement (repeat three times), then put the test tube on a magnetic stirrer and stir in an oil bath preheated at 150 °C React for 10 hours. After cooling to room temperature, add 20 mL of water to quench the reaction, extract the reaction mixture 3 times with 15 mL of a mixed solvent of petroleum ether and ethyl acetate in an equal volume ratio, wash the organic phase with 10 mL of water, dry the organic phase with anhydrous magnesium sulfate, and filter , the filtrate was concentrated under reduced pressure with a rotary evaporator to obtain a crude product, the crude product was eluted with a mixed solvent of petroleum ether and ethyl acetate (from 1:...

Embodiment 2

[0018] Using a similar synthesis method, o-diiodobenzene was substituted for o-bromoiodobenzene in Example 1 to obtain phenothiazine yields of 91%.

Embodiment 3

[0020] Using a similar synthesis method, o-chloroiodobenzene replaced o-bromoiodobenzene in Example 1 to obtain phenothiazine yields of 54%.

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PUM

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Abstract

The invention provides a catalyst-free excellent-regioselectivity weak-alkali-prommoted technique for synthesizing a phenothiazine intermediate. The method comprises the following step: in an inert atmosphere, 2-acetaminophenyl S-thioacetate and o-dihalogenated aromatic hydrocarbons directly react in the presence of a weak alkali to obtain the phenothiazine drug intermediate. The technique is green and environment-friendly, has higher reaction yield of the intermediate for most phenothiazines, and has industrialized application prospects.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and more specifically, it does not need a catalyst, and under the presence of heating and a weak base, S-acetamidophenyl thioacetate and o-dihalogenated aromatics are directly reacted to obtain a phenothiazine drug intermediate body. Background technique [0002] Phenothiazine drugs can be used as drugs for treating mental disorders, for schizophrenia or other psychotic disorders, common ones are: chlorpromazine, perphenazine, fluphenazine, thioridazine, prochlorperazine wait. Therefore, the development of the synthesis of phenothiazine drug intermediates has practical value. [0003] There are relatively few methods for synthesizing phenothiazine intermediates. Unsubstituted phenothiazines can be synthesized by diphenylamine sulfur vulcanization under the catalysis of iodine at high temperature, but a large amount of malodorous and highly toxic hydrogen sulfide is produced. However, some of its...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20
CPCC07D279/20
Inventor 曾庆乐周悦
Owner BEIJING FANBO BIOCHEM
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