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Synthetic method of iron-catalyzed phenothiazine compound

A technology of phenothiazine and synthesis method, which is applied in the field of synthesis of phenothiazine compounds, can solve the problems of slow reaction, unsuitability for mass production, limitation and the like, and achieves the effects of short reaction time, good industrialization prospect and mild conditions

Inactive Publication Date: 2015-01-28
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But expensive palladium catalysts limit the method's use in production
In 2010, Ma Dawei and others reported a phenothiazine obtained by two-step C-S, C-N coupling using o-iodoaniline and o-bromothiophenol as raw materials under the action of CuI / L-proline Compounds (Angew.Chem.Int.Ed.2010,49,1291-1294). Although this method realizes the synthesis of cheap copper-catalyzed phenothiazine, self-coupling products will appear during the synthesis process, and the two The step-by-step controlled reaction takes 72-144 hours, the reaction is slow, and it is not suitable for mass production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add N-(2-mercaptophenyl)acetamide (0.3mmol, 50.1mg), FeSO 4 ·7H 2 O (0.06mmol, 16.68mg), 1,10-linphenanthroline (0.06mmol, 10.8mg) and potassium tert-butoxide (1.2mmol, 134.4mg), protected the reaction system with nitrogen gas (exhausted three times), and used 1,2-Dibromobenzene (0.45mmol, 105.2mg) and DMF (2mL) were added to the reaction system by syringe, heated to 135°C, and stirred for 24h. After the reaction was completed, it was cooled to room temperature, 20 mL of water was added and extracted three times with ether, the organic phase was washed with water, dried with anhydrous sodium sulfate, spin-dried, and the product 10H-phenothiazine was obtained by column chromatography. Yield 70%. 1 HNMR (400MHz, DMSO-d 6 ), (ppm): 8.58 (s, 1H), 7.00-6.96 (m, 2H), 6.91-6.89 (d, J=7.6, 2H), 6.76-6.68 (m, 4H), 13 CNMR (100MHz, DMSO-d 6 ), (ppm): 142.57, 128.01, 126.70, 122.23, 116.81, 114.89, LC-MS: [M+H] + m / z = 200.0.

Embodiment 2

[0021] Adopt the method in similar embodiment 1, replace the o-dibromobenzene in embodiment 1 with o-bromoiodobenzene, o-bromochlorobenzene, o-chloroiodobenzene, o-dichlorobenzene respectively, obtain the yield of product phenothiazine respectively It's 72%, 81%, 80%, 20%.

Embodiment 3

[0023] Using a similar synthesis method, 2-bromo-4-methyliodobenzene was used instead of o-dibromobenzene in Example 1 to obtain 2-methyl-10H-phenothiazine with a yield of 19%. 1 HNMR (400MHz, DMSO-d 6 ), (ppm): 8.50(s, 1H), 6.99-6.95(m, 1H), 6.90-6.88(m, 1H), 6.79-6.67(m, 3H), 6.59-6.51(m, 2H), 2.15 (s,3H), 13 CNMR (100MHz, DMSO-d6), (ppm): 142.61, 142.48, 137.36, 127.90, 126.68, 126.49, 122.95, 122.11, 117.09, 115.57, 114.89, 113.41, 21.13. LC-MS: [M+H] + m / z = 214.1.

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Abstract

The invention provides a synthetic method of an iron-catalyzed phenothiazine compound. The synthetic method comprises the following step: in the presence of an iron salt catalyst, a ligand and an alkali, carrying out C-S coupling, C-N coupling and deacylation reaction on raw materials (N-(2-sulfydryl phenyl) acetamide and o-dibromobenzene) at a certain temperature to obtain the phenothiazine compound. The synthetic method provided by the invention is simple in operation, mild in condition, wide in application range, relatively high in yield and short in reaction time and has a good industrial prospect.

Description

technical field [0001] The invention relates to the field of chemical organic synthesis, in particular to an iron-catalyzed synthesis method of phenothiazine compounds. Background technique [0002] Phenothiazine is also called thiarazine (xanthracene) and thiodiphenylamine, and has important application value in the synthesis of medicines, dyes, organic light-emitting materials and other fields. As an excellent polymerization inhibitor for vinyl monomers, it is widely used in the production of acrylic acid, acrylate, methacrylate, and vinyl acetate. It can also be used in the fields of antioxidants, rubber anti-aging agents, livestock anthelmintics and fruit tree insecticides. Derivatives of phenothiazines have been successfully applied to the treatment of many diseases such as mental illness, heart disease, antitussive, analgesic and antipruritic. Common phenothiazines include: chlorpromazine, perphenazine, demethoxate, esmolol, trifluoperazine hydrochloride tablets, meq...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20C07D513/04
CPCC07D279/20C07D513/04
Inventor 张松林胡伟业郑松林吴三王茹张方
Owner SUZHOU UNIV
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