2-sec-Butylphenol → Fenobucarb

Participants

Reaction Steps

To a solution of 2-Sec. butylphenol (1.5 g, 0.01 mole) 0.2 ml of Et3N was added under stirring. S-methyl ester of N-methylcarbamothioic acid (1.05 g, 0.01 mole) in acetonitrile (10ml) was added dropwise over a period of 4 hrs, keeping reflux temperature. After 30 hr, acetonitrile was evaporated under vacuum. The residue was taken in dichloromethane (25 ml), washed with water and a 5% cold NaOH solution, followed by water and brine and dried over sodium sulphate. After removal of the solvent, the liquid residue obtained was further purified by distillation to give 2-Sec. butylphenyl N-methylcarbamate of the formula VI; IR: 3329 (N--H), 1730 (--COO), 1535, 1490 and 750 (aromatic); PMR (CdCl3, 90 MHz): 0.81 (3H, 1, primary methyl of side chain), 1.18 (3H, d, J=7 Hz, secondary/methyl of side chain), 1.58 (2H, m, methylene protons of side chain), 2.88 (4H, doublet overlapping a multiplet, NH--CH3 and benzylic proton), 4.97 (1H, br s, N H) and 6.95 to 7.25 (4H, m, aromatic).

Provenance & Evidence