Ethyl 3-aminobenzoate → Ethyl 3-isothiocyanatobenzoate

Participants

Reaction Steps

In 500 ml of toluene was dissolved 82.5 g of ethyl m-aminobenzoate. While stirring the solution at room temperature, 83.4 g of N,N-diethylthiocarbamoyl chloride was added dropwise to the solution over a period of about 1 hour and then the mixture was refluxed for 5 hours. The toluene was distilled off under reduced pressure, the residue thus formed was dissolved in 300 ml of ethyl acetate, and the ethyl acetate solution was washed with water. Then, ethyl acetate was distilled off under reduced pressure and the residue was further subjected to distillation under reduced pressure to provide 80 g of oily ethyl m-isothiocyanatobenzoate having a boiling point of 125° C./0.6 mm Hg at a yield of 77%.

Provenance & Evidence