Manufacture of oxazole derivatives

Details Manufacture of oxazole derivatives Manufacture of oxazole derivatives

C - Chemistry, Metallurgy

07

D

C07D 263/34 (2006.01)

Patent

CA 2228866

A process for the manufacture of a 5-cyano-4-lower alkyl-oxazole by the dehydration of a 5-carbamoyl-4-lower alkyl-oxazole comprises carrying out the dehydration with silicon tetrachloride in the presence of an amine in an organic solvent. The amine is suitably an aliphatic amine, especially a tertiary aliphatic amine, e.g. a trialkylamine, or a nitrogen-containing heteroaromatic compound, e.g. pyridine or a pyridine derivative. An aliphatic or cyclic ether, an aliphatic nitrile, an aromatic hydrocarbon or N-methylpyrrolidone is suitably used as the organic solvent. For example, 5-carbamoyl-4-methyl-oxazole is dehydrated by the process in accordance with the invention to 5-cyano-4- methyl-oxazole, which is a valuable intermediate in the synthesis of pyridoxine.

Méthode pour obtenir un 5-cyano-4-alkyl(inf.)oxazole par déshydratation d'un 5-carbamoyl-4-alkyl(inf.)oxazole, consistant à effectuer la déshydratation à l'aide de tétrachlorure de silicium en présence d'une amine, dans un solvant organique. L'amine est de nature aliphatique, surtout tertiaire, p. ex. une trialkylamine, ou un composé hétéroaromatique azoté, p. ex. une pyridine ou un dérivé de pyridine. Le solvant organique est un éther aliphatique, un éther cyclique, un nitrile aliphatique, un composé aromatique ou la N-méthylpyrrolidone. On peut ainsi déshydrater le 5-carbamoyl-4-méthyloxazole en 5-cyano-4-méthyloxazole, un intermédiaire très important pour la synthèse de la pyridoxine.

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