1-Bromohexane → HCID 70981889, compound

Participants

Reaction Steps

4,5-Dichloroimidazole (1.23 g, 9 mmol) was dissolved into 27 mL of acetonitrile. Potassium hydroxide (0.61 g, 9.9 mmol) was added and the mixture was allowed to stir for 0.5 h. 1-bromohexane (1.26 mL, 9 mmol) was added and the solution was allowed to reflux overnight. The solution was filtered hot to remove a white precipitate (presumed to be KBr) and 2-bromomethylnaphthalene (1.98 g, 9 mmol) was added and the mixture was returned to reflux overnight. The mixture was then allowed to cool to room temperature, resulting in a yellow precipitate (2.57, 65% yield). 1H NMR (500 MHz, DMSO-d6) 9.64 (1H, s, NCHN), 8.02 (4H, m, Ar), 7.57 (3H, m, Ar), 5.66 (2H, s, NCH2), 4.22 (2H, t, NCH2), 1.80 (2H, tt, CH2), 1.30 (6H, m, CH2), 0.93 (3H, t, CH3). 13C{1H} NMR (125 MHz, DMSO-d6) 136.4 (NCN), 132.8 (Ar), 132.6 (Ar), 130.0 (Ar), 128.8 (Ar), 127.8 (Ar), 127.7 (Ar), 127.6 (Ar), 126.8 (Ar), 126.7 (Ar), 125.5 (Ar), 119.1 (Ar), 51.6 (CH2), 48.3 (CH2), 30.5 (CH2), 28.0 (CH2), 24.9 (CH2), 21.8 (CH2), 13.2 (CH3). MS: m/z=332.9 (theor for C20H23Cl2N2Br1=414.17).

Provenance & Evidence