Furfurylamine → 2-(Isothiocyanatomethyl)furan

Participants

Reaction Conditions

Reaction Steps

Furfurylamine (9.71 g) is added over 30 minutes to a stirred, cooled mixture of 8.84 g of NaOH, 20 ml of CH2Cl2, 15 ml of H2O and 7.5 ml of CS2. The mixture is stirred 55 minutes in the ice bath and 600 ml of 5.25% aqueous NaOCl solution is added over 1 hour and 45 minutes (temperature is maintained at 8° C. or less). After stirring 16 hours at 20° C., the reaction mixture is extracted three times with CH2Cl2 (total volume of combined CH2Cl2 extracts is 600 ml). The CH2Cl2 extract is washed with 2×100 ml of H2O, dried with Na2SO4 and evaporated to give 12.4 g of crude furfurylisothiocyanate.

Provenance & Evidence