2-Chloro-5-nitrobenzenesulfonamide

White Solid

9.45 g 1-Chloro-4-nitrobenzene (60 mmol) was heated in 20 ml chlorosulfonic acid at 120° C. overnight. The mixture was then poured onto 400 g ice and it was extracted four times with 50-50 ml dichloromethane. The combined organic layer was washed twice with brine, dried over MgSOTo 28percent ammonia water (4.71 g, 69.2 mmol), compound 3 (4.43 g, 17.3 mmol) was added in small portions at 10 °C. When the addition was complete, the reaction was stirred at room temperature overnight. The suspension was acidified with 5 mol/L hydrochloric acid to pH 7. The white precipitate was collected by filtration to give benzenesulfonamide 4, 3.68 g, yield 90percent, m.p. 184-185 °C General Procedure VII-BFA mixture of compound VII-XIVb (4 g, 15.7 mmol) in 40 mL of aqueous ammonia was stirred at r.t. for 1 h. Then the mixture was poured into water, the precipitate solid was collected by filtration, and dried to afford compound VII-XIVc (3 g, yield 81percent). MS (ESI) m/z (M+H)EXAMPLE 17A-1 To a solution of thionyl chloride (240 mL) and 2-chloro-5-nitro-benzenesulfonic acid (104 g, 437. 6 mmol) was added N, N-DIMETHYLFORMAMIDE (2 ML) and the reaction mixture was heated up to reflux for 4 hours. The reaction mixture was then carefully quenched into water and the product was isolated by filtration. The sulfonyl chloride 2 was then dissolved in toluene and added to a mixture OF NH40H (520 mL) and tetrahydrofuran (520 ML) at-10 °C. After mixing for 1 h, the reaction was quenched by addition of 6 M HC1 to a final pH of 4. The layers were separated and the organic layer was concentrated to a slush. Pentane was added and the product was isolated by filtration and dried to give the title compound (82.6 g, 80percent).Sodium nitrite (4.96 g; 72 mmol) dissolved in water (11 mL) was added drop wise over 30 minutes to a cooled solution (−5° C.) of 2-chloro-5-nitroaniline (1; 10.00 g; 58 mmol) in 12M HCl (104 mL). While stirring at −5° C. for a further 30 minutes, a solution of copper(II) chloride dissolved in water (4 mL) was poured into acetic acid (110 mL) previously saturated with sulphur dioxide (gas). This was then added to the diazonium salt 2 solution and stirred until nitrogen gas ceased to evolve. The reaction mixture was quenched with ice-water and the subsequent precipitate formed was collected by filtration and washed with cold water. Aqueous ammonium hydroxide (35percent) (120 mL) was added to the resulting sulfonyl chloride 3 and stirred for 18 hours. The solution was then filtered and the resulting filtrate was acidified using 12M HCl to precipitate the title compound 4 (7.55 g; 55percent over 3 steps). M.p 186-187° C. (lit. 177-179° C.)To a solution of thionyl chloride (11 mL) and 2-chloro-5-nitro- benzenesulfonic acid (4.78 g, 20.1 mmol) was added N, N-dimethylformamide (0.92 μL) and the reaction mixture was heated to reflux for 4 h. Upon cooling, the reaction mixture was azeotroped with toluene (2-3 x). The sulfonyl chloride was dissolved in a minimal amount of toluene and then added to a mixture of concentrated aqueous ammonium hydroxide solution (25 mL) and tetrahydrofuran (25 mL) at -10 [0295] 2-Chloro-2-chloro-5-nitrobenzenesulfonic acid (44 mmol) was heated at reflux for 3.5 hours in a mixture of thionyl chloride (22 mL) and dimethylformamide (2 mL). After cooling the reaction mixture to room temperature, the solvents were removed under high vacuum. The crude solid was azeotroped with toluene (3×100 mL) to dryness under vacuum. The final residue was taken up in a mixture of toluene (20 mL) and tetrahydrofuran (50 mL) then cooled to 0° C. Ammonia (50 mL) was added to the stirred reaction mixture, then allowed to warns to room temperature overnight. The solution was acidified using 6 M HCl (pH 4) and extracted with ethyl acetate (3×100 mL). The combined organics were dried over MgSO-Chloronitrobenzene (10 g, 63.5 mmol) was charged into a flask, followed by addition of chlorosulfonic acid (21.1 mL, 317 mmol), and heated at 120

Molecular Weight:236.63
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:235.9658555
Monoisotopic Mass:235.9658555
Topological Polar Surface Area:114
Heavy Atom Count:14
Complexity:320
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes