4-(3-(N-methylsulfamoyl)phenyloxy)-1-nitrobenzene → 4-(3-(N-methylsulfamoyl)phenyloxy)aniline

HRID 898963Notes

Reaction equation

HRID 898963 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4]>CCOC(C)=O.[Pd]>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 236145724-(3-(N-methylsulfamoyl)phenyloxy)-1-nitrobenzene

Product 1

HCID 231372394-(3-(N-methylsulfamoyl)phenyloxy)anilineYield 25.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 4-(3-(N-methylsulfamoyl)phenyloxy)-1-nitrobenzene (0.30 g) and 10% Pd/C (0.030 g) in EtOAc (20 mL) was stirred under an H2 atmosphere (balloon) overnight. The resulting mixture was filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)aniline (0.070 g).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (30% EtOAc/70% hexane)

Sources & evidence

ORD record
ord-2192e893bfc14922a295545c6f84a15b
Source dataset
uspto-grants-2008_04
Patent number
US07351834B1

Reaction notes

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