- Comparison of photoreactions of flutamide in acetonitrile and 2-propanol solvents in the absence of cage-forming compounds
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Flutamide(2-methyl-N-[4-nitro-3-(trifluoromethylphenyl)]propanamide) is a widely used anti-cancer drug. It has been reported that photodermatosis is occasionally induced when an individual taking flutamide is exposed to sunlight. In this study, we found that flutamide undergoes different photoreactions in two different solvents: acetonitrile and 2-propanol. The photo-induced nitro-nitrite rearrangement was the predominant reaction when a flutamide solution in acetonitrile was irradiated with UV light, and phenoxy radicals and nitrogen monoxide were generated. The nitrogen monoxide recombined with the phenoxy radical at the ortho position and was oxidized by the oxygen dissolved in the acetonitrile. The final product was o-nitrophenol derivative. However, the photoreduction of the nitro group followed by solvolysis of the trifluoromethyl group was observed when a flutamide solution in 2-propanol was irradiated with UV light. The three fluorine atoms in the trifluoromethyl group were eliminated by being nucleophilically attacked by a solvent molecule, resulting in an ester bond with 2-propanol being formed.
- Watanabe, Yurie,Fukuyoshi, Shuichi,Oda, Akifumi
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- Synthesis method of drug intermediate flutamide
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The invention discloses a synthesis method of a drug intermediate flutamide. N-hexane, m-trifluoromethylaniline, isobutyric anhydride, NaOH, m-isobutyramidobenzotrifluoride, sodium hydrogen carbonateand ethyl orthosilicate are used as main raw materials; a method of combining a sol-gel method with calcination is utilized; SiO2 is used as a carrier; a perfluorosulfonic resin solution is directly dispersed on a porous SiO2 colloid serving as a skeleton; a mixing-ratio relation among raw materials is strictly explored; a catalyst for preparing the flutamide from the isobutyric anhydride, which has certain crystal form, grain size, pore structure and specific area and high mechanical strength is developed; the raw materials used by the synthesis method are according to the following mixing ratios in which a mass ratio of the isobutyric anhydride to the m-trifluoromethylaniline is 2 to 1, a volume ratio of the n-hexane to the NaOH is 2 to 1, and the volume ratio of concentrated sulfuric acid to concentrated nitric acid is 10 to 1; a preparation method of the flutamide has the characteristics of simpleness, easiness, feasibleness, short preparation period and the like, and the raw materials and the catalyst which are used in a technical process have high efficiency, wide application ranges and an excellent catalytic effect on the preparation of the flutamide from the isobutyric anhydride, are simple, convenient, quick and extremely environment-friendly, moreover, are easily recovered and can be regenerated.
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Paragraph 0008; 0010-0028
(2018/06/21)
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- Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water
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A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)·2H2O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua
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supporting information
p. 1697 - 1701
(2015/07/20)
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- Reductive acylation of nitroarenes to anilides by sodium sulfite in carboxylic acids
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A facile and efficient reductive acylation of aromatic nitro compounds to corresponding anilides using a sodium sulfite-carboxylic acid system for the first time has been reported. The sodium sulfite reagent provides the colorless reductant in combination with stoichiometric amounts of carboxylic acid and enables the formation of anilides from nitroarenes without any additives in good to excellent yields with high purities and simple work-up. Furthermore, this protocol provides a novel and complementary access to some industrially important chemicals in kilogram scale under mild conditions.
- Ghaffarzadeh, Mohammad,Akhavan, Pegah
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supporting information
p. 1417 - 1419
(2016/09/28)
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- A novel method for synthesis of flutamide on the bench-scale
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Flutamide has been synthesised conveniently in high yields and by an economically beneficial method. Benzotrifluoride was first nitrated and the product was reduced and acylated in one pot in the presence of iron powder and isobutyric acid to produce 3-trifluoroisobutyranilide. Finally, flutamide was produced by further nitration.
- Ghaffarzadeh, Mohammad,Rahbar, Sahar
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p. 200 - 201
(2014/05/06)
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- Novel and gram-scale green synthesis of flutamide
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Isobutyric acid in the presence of cyanuric chloride and N-methylmorpholine was converted into active ester 3 at 0-5°C, and it was subsequently treated with 3-aminobenzotrifluoride 4 at 25°C to furnish corresponding amide 5. This amide finally, on nitration, produced the desired product flutamide, 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide 6 in good yield. By-product 2,4,6-trihydroxy-1,3,5-triazine 7 was converted into the useful starting material cyanuric chloride 1 by refluxing with N,N-diethylamine and POCl3. Copyright Taylor & Francis Group, LLC.
- Bandgar,Sawant
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p. 859 - 864
(2007/10/03)
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