4-Amino-3-chlorobenzenesulfonamide

Under anhydrous and anaerobic conditions, Dissolve 1 mmol of sulfanilamide in 12 mL of tetrahydrofuran.Then add 2mmol NCS powder, The reaction was carried out at 40 °C for 25 h.The solvent was distilled off, the residue was extracted with 30 mL of ether, and the organic layer was washed with 5 mL of saturated potassium carbonate solution and 5 mL of saturated saline.The organic layer was dried over anhydrous sodium sulfate and subjected to column chromatography (dichloromethane:ethyl acetate 7:1).188 mg of pale yellow powder was obtained in a yield of 95percent.4-Acetamido-3-chlorobenzenesulfonamide was suspended in a mixture of water, EtOH and concentrated aqueous HCl (0.06: 1 : 0.4). The suspension was stirred and heated to 850C under nitrogen for 1 hour. After cooling to room temperature, the mixture was quenched with saturated NaHCtheta3 and extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. EPO To a mixture of THF and concentrated aqueous ammonia (2:1) was added 4-acetamido- 3-chlorobenzensulfonyl chloride. The mixture was stirred for 20 minutes at room temperature and the solvents were removed under reduced pressure. The residue was triturated with cold water. The obtained solid was collected by filtration and dried under high vacuum. 1H NMR (300 MHz, DMSO-d6) No.: 9.71 (s, 1H), 8.06-7.97 (m, 1H), 7.87 (d, J = 2.0 Hz, 1H), 7.73 (dd, J = 2.0 Hz, J2 = 8.6 Hz, 1H), 7.74 (s, 2H), 2.15 (s, 3H). MS m/z: 249 (M+H)+. Step 2: Under anhydrous and anaerobic conditions, In a 100 mL two-necked flask, 207 mg of 3-chloro-p-aminobenzenesulfonamide (1 mmol) was added, 178m g NBS powder (1mmol) and solvent acetonitrile 8mL, The reaction was carried out at 20C for 3 hours.The solvent was distilled off and the residue was extracted with 30 mL of diethyl ether. The organic layer was washed with saturated potassium carbonate solution and saturated brine.The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. The pure product was obtained in a yield of 99%.

Molecular Weight:206.65
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:205.9916763
Monoisotopic Mass:205.9916763
Topological Polar Surface Area:94.6
Heavy Atom Count:12
Complexity:249
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes