HCID 18957771, compound → HCID 18957772, compound

HRID 2379353Notes

Reaction equation

HRID 2379353 reaction equation
[CH3:1][C:2]([CH3:19])([C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)(=[O:9])=[O:8])=[O:5])[CH3:3]>[Pd].O.C(O)C>[CH3:3][C:2]([CH3:19])([C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)(=[O:9])=[O:8])=[O:5])[CH3:1]

Participants

5

Reactant 1

HCID 18957771HCID 18957771, compound

Product 1

HCID 18957772HCID 18957772, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 1-(1,1-dimethylethylcarbonylaminosulphonyl)-3-nitrobenzene (5 g, 17.5 mmol), 10% palladium on carbon (0.5 g, 10% (w/w)) in water (4 ml) and ethanol (100 ml), the title compound (3.36 g, 75%) was afforded as a pale yellow solid after recrystallisation from ethanol. mp 147°-150° C. 1H NMR (360 MHz, D6-DMSO) δ 1.07 (9H, s), 5.62 (2H, brs), 6.78 (1H, dd, J=8.0 and 2.0 Hz), 6.94 (1H, d, J=8.0 Hz), 7.08 (1H, t, J=2.0 Hz), 7.19 (1H, t, J=7.9 Hz), 11.47 (1H, brs).

Sources & evidence

ORD record
ord-fa00fcd0db3a43278763ce143657443b
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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