N-(3-nitrophenyl)sulfonylbenzamide → 3-amino-N-benzoyl-benzenesulfonamide

HRID 2379323Notes

Reaction equation

HRID 2379323 reaction equation
[C:1]1([C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)(=[O:12])=[O:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].O.C(O)C>[C:1]1([C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)(=[O:12])=[O:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 2947178N-(3-nitrophenyl)sulfonylbenzamide

Product 1

HCID 146178143-amino-N-benzoyl-benzenesulfonamideYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 1-(phenylcarbonylaminosulphonyl)-3-nitrobenzene (5.3 g, 17.3 mmol), 10% palladium on carbon (0.5 g, 9% (w/w)) in water (3 ml) and ethanol (100 ml), the title compound (4.3 g, 90%) was afforded as a yellow solid. mp 160°-162° C. 1H NMR (360 MHz, D6 -DMSO) δ 6.81 (1H, m), 7.07 (1H, m), 7.22 (2H, m), 7.48 (2H, m), 7.60 (1H, dd, J=7.4 and 7.4 Hz), 7.87 (2H, m).

Sources & evidence

ORD record
ord-9b1583421a2544ceac6d10c18a90de8e
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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