Water → HCID 23301864, compound

Participants

Reaction Steps

A mixture of 20.95 g (0.107 mole) of 4-cyanobenzyl bromide, 14.7 g (0.107 mole) K2CO3, 5.0 g KI, and 10.32 g (0.12 mole) 2-imidazolidinone in 125 ml dimethylsulfoxide was stirred at 100°-110° for 30 minutes, cooled, and poured into 400 ml cold tap water. The mixture was stirred at room temperature for 30 minutes and extracted with 250 ml chloroform. The chloroform extract was washed with 3 × 250 ml H2O, dried (MgSO4), and concentrated to dryness in vacuo to give an oily residue. Crystallization from 60 ml toluene gave 5.50 g of the crude product. Further recrystallization from toluene gave 4.34 g (20%) of the nitrile, m.p. 127°-133°. The analytical sample, m.p. 134°-136°, was obtained by recrystallization from toluene.

Provenance & Evidence