Diethyl Ether → 4-Bromo-N-(prop-2-en-1-yl)benzene-1-sulfonamide

To a solution of 4-bromobenzenesulfonamide (6.80 g 26.6 mmol) in dichloromethane (50 mL) was added allylamine (5.0 mL, 66.5 mmol) at 0° C. The clear, colorless solution was stirred at room temperature for 1 h. The reaction mixture was poured into ether (100 mL) and washed with 10% aq HCl (50 ML), water (2×50 mL), and saturated aq NaHCO3 (50 mL). The organic phase was dried (MgS04) and concentrated. The residue crystallized upon treatment with hexane to provide 7.03 g (96% yield) of the desired product as fine, white crystals. Mp: 63-65° C. (lit. 64-65° C. See Keasling, H. H.; Schumann, E. L.; Veldkamp, W. J. Med. Chem. 1965, 8, 548). 1H NMR (400 MHz, CDCl3): δ 7.77-7.72 (m, 2H), 7.69-7.64 (m, 2H), 5.71 (ddt, J=17.1, 10.2, 6.0 Hz, 1H), 5.18 (dq, J=17.1, 1.5 Hz, 1H), 5.12 (dq, J=10.2, 1.5 Hz, 1H), 4.67 (t, J=6.0 Hz, 1H), 3.61 (tt, J=6.0, 1.5 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ 139.0, 132.6, 132.4, 128.6, 127.6, 118.0, 45.7.

1. washwashed with 10% aq HCl (50 ML), water (2×50 mL), and saturated aq NaHCO3 (50 mL)
2. customThe organic phase was dried (MgS04)
3. concentrationconcentrated
4. customThe residue crystallized upon treatment with hexane

ORD record

ord-cb43ae24c7614cc991fb13f67cf98888

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323608B2