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Synthesis process of fenticonazole nitrate

A technology of fenticonazole nitrate and synthesis process, which is applied in the field of medicine and can solve problems such as strong corrosion, high chemical reactivity, and unsuitability for industrial production

Inactive Publication Date: 2018-12-28
XIANGYU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] Both method 1 and method 2 are under anhydrous and anaerobic conditions, using sodium hydride as a condensing agent to react to obtain fenticonazole, the difference is that the solvents used are different, which are hexamethylphosphoric triamide and dimethyl ethylene oxide respectively. Sulfone, although the yield is significantly improved when dimethyl sulfoxide is used, these solvents are expensive, and the chemical reactivity of the reactant sodium hydride is very high. It releases heat and hydrogen, causing combustion and explosion, and forms hydroxides when it encounters moisture and moisture. It is highly corrosive, so the required solvent must be absolutely anhydrous, and the reaction must be carried out under the protection of an inert gas, which is not suitable for industrial production.

Method used

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  • Synthesis process of fenticonazole nitrate
  • Synthesis process of fenticonazole nitrate
  • Synthesis process of fenticonazole nitrate

Examples

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Embodiment 1

[0039] The synthesis process of fenticonazole nitrate uses cheap and easy-to-obtain reagents, greatly reduces the synthesis cost, is easy to operate, has no special requirements for equipment, and is more suitable for large-scale production. For specific synthesis routes, see figure 1 .

Embodiment 2

[0041] Intermediate I: Synthesis of 4-phenylmercaptobenzaldehyde

[0042] At room temperature (25°C), put 592g of p-bromobenzaldehyde, 360g of thiophenol, 480g of potassium carbonate, 16g of CuI and 2000ml of DMF into a 5000mL reaction flask, stir and heat up to 124-128°C, react for about 6 hours, and perform TLC detection ( n-Hexane: ethyl acetate = 10:1) to the end of the reaction, drop to 90°C and filter, reduce pressure (pressure 1720Pa, temperature 85°C) and concentrate to dryness, recover DMF to obtain a viscous residue, add dichloromethane 2400ml , washed three times with water, dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated to dryness under reduced pressure, and dichloromethane was recovered, and the residue was dissolved in 240ml of a mixed solution (hexane:ethyl acetate=1:1), frozen and crystallized, filtered, The filter cake was dried under normal pressure at 25° C. to obtain 536 g of white crystalline powder with a yield of 78.3%. ...

Embodiment 3

[0044] Intermediate II: Synthesis of 4-Phenylmercaptobenzyl Alcohol

[0045] At room temperature (25°C), put 527g of 4-phenylmercaptobenzaldehyde and 2965ml of methanol into a 5000mL reaction flask, add 29.65g of sodium borohydride in three batches, stir and raise the temperature to 48°C, and react for about 1 hour. alkane: ethyl acetate = 10:1) to the end of the reaction, hydrochloric acid was added dropwise to adjust the pH to 6, and concentrated to dryness under reduced pressure (pressure 1330Pa, temperature 45°C) to recover methanol. To obtain a viscous residue, add 2200ml of dichloromethane, wash with water until neutral, dry over anhydrous magnesium sulfate, filter, concentrate the filtrate to dryness under reduced pressure (pressure 1720Pa, temperature 25°C), recover dichloromethane, and obtain light yellow crystals Sexual powder 518.7g, yield 97.3%, HPLC purity: 99.56%.

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Abstract

The invention belongs to the technical field of chemical synthesis, and discloses a synthesis process of fenticonazole nitrate. The synthesis process comprises the following steps: 1) synthesis of intermediate I:4-phenylthio-benzaldehyde; 2) synthesis of intermediate II:4-phenylthio benzyl alcohol; 3) synthesis of intermediate III:4-phenylthio benzyl chloride; 4) synthesis of crude fenticonazole nitrate; 5) refining of the fenticonazole nitrate; 6) preparation of suppository. The synthetic process is simple and feasible and suitable for popularization and use, and has broad market applicationprospects.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a synthesis process of fenticonazole nitrate. Background technique [0002] Fenticonazole nitrate, English name: Fenticonazole Nitrate; English chemical name: 1-[2-(2,4-dichlorophenyl)-2-[[4-(phenylthio)phenyl]methoxy]ethyl-1H-imidazolemononitrate; Chinese chemistry Name: 1-[2-(2,4-dichlorophenyl)-2-[[4-(phenylthio)phenyl]methoxy]ethyl-1H-imidazole nitrate; molecular formula: C 24 h 20 Cl 2 N 2 OS·HNO 3 , molecular weight: 518.4; physical and chemical properties: this product is white or off-white crystal or crystalline powder; odorless; this product is easily soluble in methanol and N, N-dimethylformamide, slightly soluble in ethanol, almost soluble in water Insoluble; the melting point of this product is 134~137°C; the specific rotation of this product is -0.10°~+0.10°. [0003] Fenticonazole nitrate has a wide range of uses in the field of medicine, and its ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60A61K31/4174A61P31/10A61K9/02
CPCC07D233/60A61K9/02A61K31/4174A61K47/44A61P31/10
Inventor 林凡友王明涛张尤乐崔靖
Owner XIANGYU PHARMA
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