A. V. Velikorodov, E. A. Shustova, S. B. Nosachev
Dec 1, 2017
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Journal
Russian Journal of Organic Chemistry
Abstract
Acetophenones containing a methoxycarbonylamino group in position 2, 3, or 4 of the aromatic ring reacted with phenylglycine in the presence of 2 equiv of iodine and 0.5 equiv of sulfanilic acid in DMSO at 100°C for 6 h to give methyl [2(3,4)-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamates. The reaction was presumed to involve intermediate formation of methyl [(iodoacetyl)phenyl]carbamate. This was confirmed by the isolation of methyl [2-(iodoacetyl)phenyl]carbamate in the reaction of methyl (2-acetylphenyl)carbamate with iodine in glacial acetic acid and its subsequent transformation to methyl [2-(2-phenyl-1,3-oxazol-5-yl)-phenyl]carbamate.