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Catalyst-free synthesis of phenothiazine drug intermediates

A phenothiazine and intermediate technology, applied in the field of drug synthesis, can solve problems such as complex aniline structure, and achieve the effects of cheap and easily available raw materials, short time and mild reaction conditions

Active Publication Date: 2018-04-06
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 to carry out two consecutive C-S couplings in a reactor to obtain phenothiazine ( Synlett , 2011, (1), 134-138); however, its raw material 2-bromo-N-(2-iodophenyl)aniline has a complex structure and needs to be synthesized in multiple steps to obtain

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Take a dry, ground-mouth test tube with a magnetic stirring bar, add 2 mmol of cesium carbonate, 0.5 mmol of S-2-acetamidophenyl thioacetate, o-bromoiodobenzene, 2 mL of N,N-dimethylformaldehyde Amide, fasten and seal with a rubber anti-port stopper, evacuate with an oil pump on the Schlenk vacuum line, and then fill with argon for replacement (repeat three times), then put the test tube on a magnetic stirrer and preheat an oil bath at 150°C The reaction was stirred in the pot for 10 hours. After cooling to room temperature, 20 mL of water was added to quench the reaction, and the reaction mixture was extracted three times with 15 mL of a mixed solvent of petroleum ether and ethyl acetate, and the organic phase was washed with 10 mL of water, and the organic phase was washed with anhydrous magnesium sulfate Dry, filter, and concentrate the filtrate under reduced pressure with a rotary evaporator to obtain a crude product. The crude product is eluted with a mixed solvent...

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 Patents(China)
IPC IPC(8): C07D279/20
CPCC07D279/20
Inventor 曾庆乐周悦
Owner BEIJING FANBO BIOCHEM