Benzoyl chloride → Benzoyl isothiocyanate

Temperature

12.5 °C

Benzoyl isothiocyanate was prepared as a starting material for benzoyl thiourea and derivates thereof. In a 500 mL three-neck round-bottom flask (“RBF”), fitted with a condenser, thermo-probe, sealed system nitrogen purge, pressure-equilibrated addition funnel and mechanical stirrer, were placed solid ammonium thiocyanate (16.9 g, 0.22 mol) and dichloromethane (100 mL). The stirred mixture was cooled in an ice-water bath to a temperature of about 10-15° C. To the stirred mixture was added a solution of benzoyl chloride (28.4 g, 0.2 mol) in dichloromethane (50 mL) over a period of time of 20 minutes and the reaction mixture was warmed to a temperature near reflux (39° C.) for a period of time of 1 hour. Reaction completion was confirmed by FT-IR analysis. The solution was then cooled to a temperature of about 10-15° C. The solution can be concentrated to an oil to provide the benzoyl isothiocyanate. A boiling point of 128-131° C. at 15 mm Hg was measured.

1. customIn a 500 mL three-neck round-bottom flask (“RBF”), fitted with a condenser
2. customthermo-probe, sealed system nitrogen
3. custompurge
4. custompressure-equilibrated addition funnel and mechanical stirrer, were placed
5. temperaturethe reaction mixture was warmed to a temperature
6. temperaturenear reflux (39° C.) for a period of time of 1 hour
7. customReaction completion
8. temperatureThe solution was then cooled to a temperature of about 10-15° C
9. concentrationThe solution can be concentrated to an oil

ORD record

ord-082ce407e53d48b68ee4aad6a587f862

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371473B2