Carbon Disulfide → 2-(2-Isothiocyanatoethyl)thiophene

Temperature

0 °C

Thiopene ethylamine (4.60 mL, 39.31 mmol) and triethyl amine (5.00 mL, 39.31 mmol) were dissolved in 1,2-dichloroethane (25 mL), and the resulting mixture was cooled to 0° C. A solution of carbon disulfide (2.36 mL, 39.31 mmol) in 1,2-dichloroethane (50 mL) was added dropwise thereto over 15 min. The reaction mixture was allowed to warm to room temperature and re-cooled to 0° C., to which ethyl chloroformate (4.27 mL, 31.39 mmol) was added dropwise. The reaction mixture was stirred at room temperature for about 1-2 h, and water (150 mL) and aqueous 2N sodium hydroxide (75 mL) were sequentially added thereto. The resulting mixture was extracted with dichloromethane. The extract was washed with water and brine, dried over sodium sulfate, and concentrated, to obtain the yellow title compound in a liquid form (5.37 g, 80.75%).

1. temperatureto warm to room temperature
2. additionwas added dropwise
3. extractionThe resulting mixture was extracted with dichloromethane
4. washThe extract was washed with water and brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated

ORD record

ord-d8688be4626044dc953fffbd628dbc8b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648111B2