N-(3-Methoxyphenyl)-4-nitrobenzenesulfonaMide, 97% synthesis

Yield:16936-99-5 98%

Reaction Conditions:

with pyridine in dichloromethane at 20; for 24 h;

Steps:

4 Example 4 N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (21)

Example 4
N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (21)
To a solution of m-anisidine (2ml, 15 mmol) in DCM (40 mL) were subsequently added dropwise dry pyridine (1.15 mL, 15 mmol) and a solution of 4-nitrobenzenesulfonyl chloride (4.54 g, 14.6 mmol) in DCM (40 mL).
After 24 hours of stirring at room temperature, the reaction mixture was quenched with H₂O (80mL).
After extraction three times with DCM, the organic layer was washed with an aqueous solution of 10% K₂CO₃ (60mL), and a saturated aqueous solution of NaCl (60mL).
After drying with MgSO₄, filtration and concentration under vacuum, the crude was purified by chromatography over silica gel (PE/EtOAc: 90/10 to 0/100) affording the expected compound (21) as a yellow solid (4.53 g, 14.7 mmol) with 98% yield. (Rf = 0.58 (PE/EtOAc: 5/5); mp = 119.4°C).
¹H NMR (300MHz, CDCl₃): δ 8.27 (dt, J_2-2'= 2,1Hz, J_2-1= 9,0Hz, 2H, H₂ and H_2'), 7.97 (dt, J_1-1'=2,1Hz, J_1-2=9,0Hz, 2H, H₁ and H_1'), 7.15 (m, 1H,H₇), 7.09 (s, 1H, H₃), 6.69 (m, 2H, H₄ and H₆), 6.62 (m,1H, H₅), 3.75 (s, 3H, H₈) ¹³C NMR (75MHz, CDCl₃) δ 160.6, 150.4, 144.6, 136.7 (C^IV Ar) 130.6 (C₇), 128.7 (C₁ and C₁), 124.4 (C₂ and C_2'), 114.0 (C₅), 121.5 (C₅), 111.7, 108.1 (C₄ and C₆), 55.5 (C₈) MS (El,m/z): [M^+·] = 308.0 HRMS: Calculated for [M+H]⁺ 309.0537; Measured: 309.0540. IR (cm^-1): 3245 (vNH), 3113 (v=C-H), 1528 (v NO₂), 1306 (v_as SO₂)

References:

EP3412652,2018,A1 Location in patent:Paragraph 0069-0070