1-Naphthol → Carbaryl

Participants

Reaction Steps

To a solution of 1-naphthol (1.44 g, 0.01 mole) and S-methyl ester of N-methylcarbamothioic acid (1.575 g, 0.015 mole) in benzene (6 ml) there was added sodium (0.15 g) and the mixture was refluxed for 20 hrs. The reaction mixture was cooled and washed with water and a cold 5% NaOH solution followed by water and brine and then dried. The removal of solvent afforded the solid which was further purified by crystallization to furnish 1-naphthyl N-methylcarbamate of the formula VII, m.p. 140°-141° C., IR: 3305 (N--H), 1715 (--COO--), 1600, 1540, 770 (aromatic): PMR (CdCl3, 90 MHz), 2.86 (3H, d, J=1Hz, NH--CH3, 5.14 (1H, hr. s, N--H) and 7.17 to 8 (7H, m, aromatic).

Provenance & Evidence