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- W2394395063 abstract "Objective To optimize the synthetic method of ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate(4),a key intermediate for the synthesis of febuxostat.Methods 4-Hydroxy-benzonitrile was treated with sodium hydrogen sulfide and anhydrous magnesium chloride in dimethylformamide to give thioamide,which was then directly cyclized with ethyl 2-chloroacetoacetate without separation to give ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate(2) in one-pot;then 2 was formylated with Duff reaction adopting hexamethylenetetramine in trifluoroacetic acid to give ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate(3);finally,the target compound was obtained by the treatment of 3 with hydroxylamine hydrochloride and sodium formate in formic acid.Results The key intermediate 4 for the synthesis of febuxostat was synthesized via a four-step procedure in a total yield of 22.6% and its structure was confirmed by 1H-NMR and ESI-MS.Conclusions The improved process does not need column chromatography to purify and the end product is very suitable for industrial preparation." @default.
- W2394395063 created "2016-06-24" @default.
- W2394395063 creator A5078003697 @default.
- W2394395063 date "2010-01-01" @default.
- W2394395063 modified "2023-09-28" @default.
- W2394395063 title "Synthesis of ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate" @default.
- W2394395063 hasPublicationYear "2010" @default.
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