3-Hydroxy-N-(4-Methoxybenzyl)-4-Nitro-N-(Thiazol-2-Yl)Benzenesulfonamide → HCID 89761412, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:11]([N:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CC(O)=O.[Fe]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([S:11]([N:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:12])=[O:13])=[CH:3][C:2]=1[OH:1]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-hydroxy-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide (9 g, 21.3 mmol) in AcOH (70 ml) was added Fe-powder (5.98 g, 106.0 mmol, Qualigens) and the resulting suspension was stirred at 70° C. for 2 h. The mixture was cooled to 25° C. The organic compound was extracted with EtOAc, washed with saturated aqueous solution of NaHCO3, dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel chromatography using a gradient of 0-50% EtOAc in hexanes as eluent to afford 5.5 g of 4-amino-3-hydroxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)benzenesulfonamide (INTERMEDIATE AD) as off white solid in 66.2% yield. 1H-NMR (400 MHz, DMSO): δ 9.82 (s, 1H), 7.37 (s, 1H), 7.29 (m, 1H), 7.21-7.25 (m, 2H), 7.08-7.09 (dd, 1H), 7.06 (s, 1H), 6.84 (d, J=8.8 Hz, 2H), 6.62 (d, J=8.4 Hz, 1H), 5.67 (s, 2H), 4.91 (s, 2H), 3.70 (s, 3H); m/z (ESI, positive ion) 392.1 (M+H).
Workup
- temperatureThe mixture was cooled to 25° C
- extractionThe organic compound was extracted with EtOAc
- washwashed with saturated aqueous solution of NaHCO3
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe resulting residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-4ca4ea8eaeda48c0b1df62540af05d56
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346798B2
Reaction notes
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