Diethyl Ether → 1-(Methylsulphonylaminocarbonyl)-3-aminobenzene

HRID 2379330Notes

Reaction equation

HRID 2379330 reaction equation
[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:7])(=[O:4])=[O:3].C(OCC)C>[Pd].O.C(O)C>[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)=[O:7])(=[O:4])=[O:3]

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

Product 1

HCID 212017011-(Methylsulphonylaminocarbonyl)-3-aminobenzeneYield 84.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In the same way as that described in Example 11, Step 2, using 1-(methylsulphonylaminocarbonyl)-3-nitrobenzene (4 g, 16 mmol), 10% palladium on carbon (0.5 g, 12.5% (w/w)) in water (5 ml) and ethanol (100 ml), the title compound (2.9 g, 83%) was afforded as a tan powder after trituration with diethyl ether. mp 153°-155° C. 1H NMR (360 MHz, D6 -DMSO) δ 3.3 (3H, s), 6.79 (1H, d, J=7.7 Hz), 7.05 (1H, d, J=7.7 Hz), 7.08 (1H, d, J=1.9 Hz), 7.13 (1H, dd, J=7.7 and 7.7 Hz).

Sources & evidence

ORD record
ord-f700c53d59844b17a941b086d4e92a33
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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