2-amino-N,N-dimethylbenzenesulfonamide

N, N-Dimethyl-2-nitrobenzenesulfonamide (2.5 g, 10.9 mmol) was dissolved in methanol (100 mL), and Pd/C (250 mg) was added. N, N-dimethyl-2-nitrobenzenesulfonamide (2g, 8.7mmol) dissolved in methanol (100 mL) was added palladium on carbon (200mg) then reacted at 25°C for 12 hours. Filtered and the solvent was removed by rotary evaporation to give the product (1.5g, 86percent yield).To a 50mL round bottom flask was added [CAC12] (30.9mg, 0. [28MMOL)] and H20 [(1ML).] To this stirred solution was added Zn-dust (931.2mg, 14. [2MMOL), ] followed by a [SOLUTION OF 2-NITRO-(N, N-DIMETHYL) PHENYLSULPHONAMIDE] (100mg, 0. [43MMOL)] in 78percent EtOH. The resultant mixture was [REFLUXED] for 1.5 hours. The solution was filtered hot over a pad of celite and then concentrated. The residue was taken up in [CH2CI2] and sequentially washed with water and brine. The organic phase was dried over [MGS04, ] filtered and concentrated. The crude product was purified by an SPE tube using Hexanes: EtOAc (99: 1 to 70: 30) to yield the title compound as a yellow oil (38.7mg, 45percent).C18-2 1.8g of compound was dissolved in methanol, palladium on carbon catalyst was added 180mg, substituted with hydrogen and stirred at room temperature overnight, TLC showed the reaction was complete, filtered through Celite, and concentrated to give a brown solid 1.1g.N, N-dimethyl-2-nitrobenzenesulfonamide was combined with zinc and ammonium chloride in methanol under the reaction conditions shown to afford 2-amino-N, N- dimethylbenzenesulfonamide in 99% yieldN, N-Dimethyl-2-nitrobenzenesulfonamide (2.5 g, 10.9 mmol) was dissolved in methanol (100 mL), and Pd/C (250 mg) was added. Hydrogen gas was introduced, and the resultant mixture was stirred at room temperature for 12 h. After the reaction, Pd/C was removed by filtration. The solvent was removed by rotary evaporation to obtain the product (2 g, yield: 92%).N, N-dimethyl-2-nitrobenzenesulfonamide (2g, 8.7mmol) dissolved in methanol (100 mL) was added palladium on carbon (200mg) then reacted at 25C for 12 hours. Filtered and the solvent was removed by rotary evaporation to give the product (1.5g, 86% yield).To a 50mL round bottom flask was added [CAC12] (30.9mg, 0. [28MMOL)] and H20 [(1ML).] To this stirred solution was added Zn-dust (931.2mg, 14. [2MMOL), ] followed by a [SOLUTION OF 2-NITRO-(N, N-DIMETHYL) PHENYLSULPHONAMIDE] (100mg, 0. [43MMOL)] in 78% EtOH. The resultant mixture was [REFLUXED] for 1.5 hours. The solution was filtered hot over a pad of celite and then concentrated. The residue was taken up in [CH2CI2] and sequentially washed with water and brine. The organic phase was dried over [MGS04, ] filtered and concentrated. The crude product was purified by an SPE tube using Hexanes: EtOAc (99: 1 to 70: 30) to yield the title compound as a yellow oil (38.7mg, 45%).General procedure: To a solution of intermediate sm-8 (1.0 eq) in MeOH was added Pd/C. The reaction mixture was stirred at 50 C. under 50 psi of H2 for 7 h. TLC indicated starting material had disappeared. The mixture was filtered, and the filtrate was concentrated to afford compound I (yield: 8991%).C18-2 1.8g of compound was dissolved in methanol, palladium on carbon catalyst was added 180mg, substituted with hydrogen and stirred at room temperature overnight, TLC showed the reaction was complete, filtered through Celite, and concentrated to give a brown solid 1.1g.

Molecular Weight:200.26
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:200.06194880
Monoisotopic Mass:200.06194880
Topological Polar Surface Area:71.8
Heavy Atom Count:13
Complexity:256
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes