Imidazole → HCID 86691644, compound

Participants

Reaction Steps

To a stirred solution of β-hydroxyoctadecanenitrile (4.5 g, 15.99 mmol), TEA (2.9 ml, 20.78 mmol) and DMAP (0.19 g, 1.59 mmol) in dry DCM (70 ml) cooled to 0° C., was added methanesulfonyl chloride (1.3 ml, 16.78 mmol) under N2. After allowing the reaction mixture to warm to room temperature, stirring was continued for another 2 hours. The reaction mixture was diluted with DCM (100 ml), the organic layer was washed with 1N HCl, water and brine solution, dried over MgSO4 and concentrated under reduced pressure. This crude compound was mixed with imidazole (2.18 g, 31.97 mmol) and heated at 70° C. for 16 hours under N2. The crude product was purified by silica gel column (2% MeOH in DCM) to give 13-(1H-imidazol-1-yl)octadecanenitrile as a light yellow liquid (1.64 g, 32%).

Provenance & Evidence