Ethanol → HCID 15670597, compound

Participants

Reaction Steps

A mixture of 2-naphthyloxyacetaldehyde hydrate (9.85 g), benzyloxyamine (5.94 g) and ethanol (100 ml) was stirred overnight under nitrogen to precipitate 11.21 g of the protected oxime, m.pt. 68°-69.5° C. The oxime (10.1 g) in acetic acid (100 ml) was reduced with sodium cyanoborohydride, then the isolated O-benzyl hydroxylamine, without purification, was treated with phenyl isocyanate (1 equivalent) in toluene for 4 hours at 110° C. The product had m.pt. 75°-77° C. after chromatography over silica gel (elution with methylene chloride) and recrystallization from SVM. Hydrogenation of the last-mentioned O-benzylhydroxyurea over 5% palladium on charcoal in ethanol containing a few drops of acetic acid provided 1-Hydroxy-1-[2-(2-naphthyloxy)ethyl]-3-phenylurea, m.pt. 165°-167° C. (from ethanol).

Provenance & Evidence