3-Bromomethylbenzenesulfonamide

1.48 g (7.90 mmol)) 3-(hydroxymethyl)benzenesulfonamide were suspended in 25 ml dichloromethane and 2.35 g (8.69 mmol) phosphorus tribromide were added at 20 °C. The mixture was stirred overnight. Water was added carefully and the organic phase separated. The aqueous phase was two times extracted with dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated in vacuo.Yield: 1.9 g (94 percent) 3-(bromomethyl)benzenesulfonamide as raw product, which was pure enough for the next step.84 mg of a dispersion of sodium hydride in mineral oil (2 mmol) was washed two times with dry THF. 3 mL of THF was added to the sodium hydride, then 1 mL 2, 2, 2-trifluoroethanthiol and 1 mmol (250mg) of 3-bromomethyl-benzenesulfonamide were added. The reaction mixture was stirred at room temperature overnight. After the reaction was completed it was quenched with 3 mL of water. The mixture was then extracted three times with ethyl acetate, the combined organic layers are washed with brine and dried over Na2S04. The organic layers are dried under reduced pressure to yield a white crude product. The crude product was further purified by column chromatography (ethyl acetate/petroleum ether 1+1 ) and recrystallization from EtOH to yield 135 mg of white powder (61 % yield). 1H NMR (200 MHz, MeOD) d 7.90 (s, 1 H), 7.90 - 7.75 (m, 1 H), 7.65 - 7.41 (m, 2H), 3.97 (s, 2H), 3.16 (q, J = 10.2 Hz, 2H). 13C NMR (50 MHz, MeOD) d 145.5, 139.9, 133.8, 130.4, 127.7 (d, J = 275.4 Hz), 127.6, 126.2, 37.2, 33.85 (q, J = 32.7 Hz). MS m/z 285625 mg (2.50 mmol) To a solution of cis-4-amino-1-(3-methoxyphenyl)-cyclohexanecarbonitrile (30.8 mg, 0.13 mmol) and N-methylmorpholine (73.5 muL, 0.67 mmol) in dimethylformamide, a solution of 1.48 g (7.90 mmol)) 3-(hydroxymethyl)benzenesulfonamide were suspended in 25 ml dichloromethane and 2.35 g (8.69 mmol) phosphorus tribromide were added at 20 C. The mixture was stirred overnight. Water was added carefully and the organic phase separated. The aqueous phase was two times extracted with dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated in vacuo.Yield: 1.9 g (94 %) To a solution of 3-(hydroxymethyl)benzenesulfonamide (25 mg, 0.13 mmol) in dichloromethane (4 mL), a solution of phosphorus tribromide (76.0 mg, 0.28 mmol) in dichloromethane (1 mL) was added, and then the mixture was stirred overnight at room temperature. The reaction mixture was cooled at 0C, and water, saturated aqueous sodium hydrogencarbonate was added thereto, and then the mixture was extracted with ethyl acetate twice, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to give the title compound. The title compound was applied to the next step without further purification. 1H-NMR delta (DMSO-d6) 4.79 (2H, s), 7.41 (2H, br), 7.56 (1H, dd, J=7.71, 7.70 Hz), 7.66 (1H, d, J=7.88 Hz), 7.75 (1H, d, J=7.70 Hz), 7.89 (1H, s).

Molecular Weight:250.12
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:248.94591
Monoisotopic Mass:248.94591
Topological Polar Surface Area:68.5
Heavy Atom Count:12
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes