3-Pyridinemethanol → Carbamic acid, (4-(methylthio)phenyl)-, 3-pyridinylmethyl ester

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Reaction Steps

To a solution of 4.4 g. (0.04 mole) of 3-pyridylcarbinol in 50 ml. of benzene containing 0.1 g. of Dabco catalyst was added, dropwise, a solution of 6.6 g. (0.04 mole) of p-methylthiophenyl isocyanate (New Haven Chemicals) in 50 ml. of benzene. During the addition a white solid separated and the temperature rose from 23°C. to 34°C. The mixture was stirred at ambient temperature for 16 hrs. and the product was filtered off. After oven-drying in vacuo there was obtained 10.4 g. melting at 133° -135°C. This is a 95% yield of 3-pyridylmethyl N-(4'-methylthiophenyl)-carbamate.

Provenance & Evidence