Sodium Hydroxide → HCID 66585000, compound

Participants

Reaction Steps

To a solution of 51.6 g (254 mmol) of 5-chloro-4-phenyl-1H-pyrrole-3-carbonitrile in 400 ml of acetonitrile are added 20.4 g (509 mmol) of finely ground sodium hydroxide and 3.46 g (10.2 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 68.5 g (255 mmol) of tert-butyl(2-bromo-ethyl)carbamate (CAS 39684-80-5), and the mixture is then stirred for 4 hours at reflux. [After cooling, the solvent is evaporated off under reduced pressure, the residue is taken up in water and the product is extracted with ethyl acetate.] The organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give 67.9 g of tert-butyl{2-[2-chloro-4-cyano-3-phenyl-1H-pyrrol-1-yl]ethyl}carbamate in the form of a white powder after recrystallizing from acetonitrile, filtering off and drying.

Provenance & Evidence