1-Chloropropane → HCID 21041471, compound

Participants

Reaction Conditions

Reaction Steps

To 4-chlorobenzonitrile (5 g) in dry N,N-dimethylformamide (50 mL), under nitrogen, was added sodium sulphide (3.11 g), and the stirred mixture heated in an oil bath at 130° C. for 48 h. The mixture was cooled to room temperature, 1-chloropropane (4.0 mL) added and stirring continued for 12 h. The mixture was cooled in an ice-water bath and “OXONE” (34 g) added with stirring. The water bath was removed after 2 h, and the mixture stirred at room temperature for 14 h. The reaction mixture was then diluted with an equal volume of ethyl acetate, solids removed by filtration, and solvent stripped at reduced pressure. The residue was chromatographed on silica gel, eluent 15 to 30% ethyl acetate in isohexane, and the title compound crystallised from isohexane as a white solid. 1H NMR (360 MHz, CDCl3) δ 8.05 (2H, d, J=8.1 Hz), 7.88 (2H, d, J=8.3 Hz), 3.10 (2H, m), 1.76 (2H, m), 1.02 (3H, t, J=7.4 Hz).

Provenance & Evidence