2-Propanesulfonyl chloride → HCID 74079905, compound

Participants

Reaction Steps

(2R)-2-(4-Aminophenyl)propanamide (0.5 g, 3.05 mmol) was dissolved in pyridine (2 mL) and 2-propanesulfonyl chloride (0.53 mL, 3.66 mmol) was added. The resulting solution was refluxed for 4 h and left overnight at room temperature. After the complete disappearance of the starting amide, the solution was diluted with Et2O (10 mL) and the organic layer washed with 1N HCl (2×5 mL), with H2O (2×5 mL), dried over Na2SO4, filtered and evaporated under vacuum to give (2R)-2-{(4-[(isopropylsulfonyl)amino]phenyl}propanamide as pale yellow solid (667 mg, 2.47 mmol). Yield 81%. mp 125-127° C.; [α]D25 (c=0.3, CH3OH): −12.7°; 1H-NMR (DMSO-d6) δ 9.65 (bs, 1H, SO2NH), 7.40 (bs, 1H, CONH2), 7.25 (d, 2H, J=7 Hz), 7.12 (d, 2H, J=7 Hz), 6.80 (bs, 1H, CONH2), 3.52 (q, 1H, J=7 Hz), 3.15 (m, 1H), 1.22 (d, 3H, J=7 Hz), 1.18 (d, 6H, J=7 Hz).

Provenance & Evidence