4-Hydroxybenzoic Acid → HCID 58453271, compound

Participants

Reaction Conditions

Reaction Steps

N-(3,5-dichlorophenyl)-N-((5-oxo-2,5-dihydro-1H-pyrazol-3-yl)methyl)benzenesulfonamide (398 mg, 1 mmol) and 4-hydroxybenzoic acid (800 mg, 5.8 mmol, 200% weight) were added to a solution of HBr (48% in H2O, 4 mL) and AcOH (4 mL). After the resulting suspension was stirred at 100° C. for 2 h, the reaction mixture was partitioned between 1N HCl (10 mL) and ethyl acetate (30 mL×2). The collected organic layers were combined, dried over Na2SO4, filtered, and concentrated. The residue was subjected to column chromatography eluting with a mixture of MeOH and dichloromethane (5% MeOH) to afford 2 (142 mg, 55% yield) as a white solid. 1H NMR (DMSO-d6, 500 MHz): δ=6.65 (t, J=5.5 Hz, 1H), 6.61 (s, 1H), 6.59, (s, 2H), 5.35 (s, 1H), 4.10 (d, J=5.0 Hz, 2H); 13C NMR (DMSO-d6, 125 MHz): δ=150.7, 134.3X2, 114.6, 110.4X2 ppm; MS (ESI): m/z 280.0 [M+Na]+; CHN calculated for C10H9Cl2N3O: C, 46.53; H, 3.51; N, 16.28. found: C, 46.44; H, 3.61; N, 16.36.

Provenance & Evidence