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ChemicalBook CAS DataBase List N-(3-Methoxyphenyl)-4-nitrobenzenesulfonaMide, 97%
16936-99-5

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

1synthesis methods
-

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, J2-2'= 2,1Hz, J2-1= 9,0Hz, 2H, H2 and H2'), 7.97 (dt, J1-1'=2,1Hz, J1-2=9,0Hz, 2H, H1 and H1'), 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 (CIV Ar) 130.6 (C7), 128.7 (C1 and C1), 124.4 (C2 and C2'), 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 (vas SO2)

References:

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