Acetonitrile → HCID 1947910, compound

Participants

Reaction Steps

One equivalent of dansyl chloride (7) was added to a solution containing 2 equivalents of both butylamine and potassium carbonate in 1:1 acetonitrile:water. Solution was stirred at room temperature for 1.5 hrs. Acetonitrile was then removed and water residue extracted with ethyl acetate. The organic solution washed with 5% sodium bicarbonate, 2M citric acid and brine. Solution was dried over magnesium sulfate, filtered and solvent removed by flash evaporation. Crude was dissolved in minimal amount of ethyl acetate and hexane was added until cloudiness. Solution was stored in the refrigerator for 2 hrs. The precipitate was collected by suction filtration, washed with hexane and dried on the pump. ESI-MS and 1H-NMR were consistent with structure 8, which is (n-butyl dansylamide; BDA): 1H-NMR (CDCl3, =ppm): 8.55 (1H, d); 8.30 (2H, dd); 7.55 (2H, m); 7.20 (1H, d); 4.80 (1H, t); 2.90 (8H, m); 1.35 (2H, m). 1.20 (2H, m); 0.70 (3H, t). ESI-MS: Calc. m/z=306.4. Found m/z+H+=307.4.

Provenance & Evidence