Butyryl chloride → HCID 21997649, compound

Participants

Reaction Conditions

Reaction Steps

(2-Amino-4-trifluoromethylphenylsulfanyl)acetonitrile (1.33 g) dissolved in dichloromethane (5 ml) was stirred on an ice bath at 0° C. Diisopropylethylamine (1 ml) and butyric acid chloride (0.9 ml) was added, and the resulting solution was allowed to reach room temperature. After 22 h more butyric acid chloride (0.9 ml) and DMAP (0.70 g) were added at 0° C. and stirring was continued at 40° C. for 24 h. The cold mixture was diluted with dichloromethane (20 ml), extracted with saturated aqueous sodium bicarbonate (10 ml), washed with water (2×50 ml), dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/heptane 1:1 as eluent. The title compound was obtained as a sirup. Yield 1.72 g (100%). The compound could be crystallised from ethyl acetate/heptane, mp 88.5-89.5° C.; El SP/MS: 302 (M+). 1H-NMR(CDCl3) δ (ppm): 8.85 (br, 1H), 8.38 (br, 1H), 7.28 (d, 1H), 7.38 (dd, 1H), 3.50 (s, 2H), 2.46 (t, 2H), 1.82 (sextet), 1.03 (t, 3H).

Provenance & Evidence