Potassium Cyanide → 1,3-benzothiazole-2-carbonitrile

Temperature

80 °C

A suspension of potassium cyanide (1.50 g, 23.0 mmol) in dimethylsulfoxide (DMSO, 100 mL) was prepared in a 1-L 3-necked flask fitted with a reflux condenser, a heating mantle and an internal temperature probe. The 2-chlorobenzothiazole (2.6 g, 2.0 mL, 15.3 mmol) was added to the reaction flask via pipet and the reaction was heated at 80° C. (internal temperature). The reaction was monitored periodically by TLC (9:1 heptane-ethyl acetate). After 5 hours the reaction appeared to be about 50% complete. After 17 hours the reaction was judged complete by TLC analysis. The reaction mixture was allowed to cool to room temperature and was then extracted with ether (5×100 mL). The extracts were dried over sodium sulfate and concentrated to give a yellow-orange solid. The crude solid was purified on silica gel (100 g) using 9:1 heptane-ethyl acetate. Fractions containing product were pooled and concentrated to give 1.4 g (57%) of the desired product as a yellow-orange solid. The structure was confirmed by 1H NMR analysis in DMSO-d6.

1. customwas prepared in a 1-L 3-necked flask
2. customfitted with a reflux condenser
3. waitAfter 17 hours the reaction was judged complete by TLC analysis
4. temperatureto cool to room temperature
5. extractionwas then extracted with ether (5×100 mL)
6. dry with materialThe extracts were dried over sodium sulfate
7. concentrationconcentrated
8. customto give a yellow-orange solid
9. customThe crude solid was purified on silica gel (100 g)
10. additionFractions containing product
11. concentrationconcentrated

ORD record

ord-f8e6d417c5434b7a8123d6507e0b7d56

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106052B2