HCID 19605551, compound → HCID 19605469, compound

HRID 1603619Notes

Reaction equation

HRID 1603619 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:7]=1)[C:3](=[O:5])[CH3:4]>C(O)C.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([C:8]2[CH:7]=[C:6]([N:2]([CH3:1])[C:3](=[O:5])[CH3:4])[CH:11]=[CH:10][CH:9]=2)(=[O:13])=[O:14])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 19605551HCID 19605551, compound

Product 1

HCID 19605469HCID 19605469, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.50 g (0.00448 mol) of N-methyl-N-[3-(4-nitrobenzenesulphonyl)-phenyl]-acetamide were suspended in 150 ml of ethanol, treated with 0.15 g of Pd/C (10%) and stirred in a H2 atmosphere at room temperature under normal pressure for 2 hrs. Then, the catalyst was filtered off, the filtrate was freed from solvent and the residue was chromatographed on silica gel with ethyl acetate/hexane 2:1. There were obtained 1.19 g (87%) of N-[3-(4-amino-benzenesulphonyl)-phenyl]-N-methyl-acetamide as white crystals; m.p.: 178-180° C.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 2:1

Sources & evidence

ORD record
ord-deb6e688b67946a4af6fe386f4c807a8
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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