Toluene → HCID 18473540, compound

Participants

Reaction Conditions

Reaction Steps

82.3 g (372 mmoles) of benzylamine were dissolved in 10 ml of toluene and added at 15-20° C. (with cooling) within 20 minutes to an emulsion of 22.5 ml (372 mmoles) of carbon disulfide and 14.88 g (372) mmoles) of NaOH in 52 ml of water. The reaction mixture was heated to 75-80° C. for 1 hour and cooled to 40° C. Within 15 minutes, 35.4 ml (372 mmoles) ethyl chloroformate were added at 40-45° C. The emulsion was brought to about pH 8 with 2N NaOH and heated to 55-60° C., gas formation ceased after about 10 hours keeping the pH at 8 with 2N NaOH (total about 8 ml). The organic layer was collected and the solvent evaporated: 96.3 g (98.3%) of benzyl isothiocyanate.

Provenance & Evidence