Carbon Disulfide → 2-(2-Isothiocyanatoethyl)-1-methylpyrrolidine

Temperatur

0 °C

A mixture of carbon disulfide (0.996 mL, 16.57 mmol) in water (5 mL) was cooled to 0° C. Then 2-(2-aminoethyl)-1-methylpyrrolidine (2.4 mL, 16.57 mmol) was added over 45 minutes. The resulting mixture was maintained at 0° C. for an additional 30 minutes and then the cooling was discontinued. Next, ethyl chloroformate (1.58 mL, 16.57 mmol) was added over a 1 h period. The resulting mixture was maintained at room temperature for an additional 30 minutes and then made basic with saturated sodium hydrogen carbonate in water. The mixture was extracted with diethyl ether (2×50 mL). The extracts were combined, washed with brine (15 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give a pale yellow oil. The oil was purified by vacuum distillation to give 1.22 g of 2-(2-isothiocyanatoethyl)-1-methylpyrrolidine.

1. temperatureThe resulting mixture was maintained at 0° C. for an additional 30 minutes
2. temperatureThe resulting mixture was maintained at room temperature for an additional 30 minutes
3. extractionThe mixture was extracted with diethyl ether (2×50 mL)
4. washwashed with brine (15 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a pale yellow oil
9. distillationThe oil was purified by vacuum distillation

ORD-Eintrag

ord-a3386d6f29e44d2a8fa2b0fb1a07ae9a

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06699866B2