Acetic Acid → Benzenamine, 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)-
Reaction equation
[CH3:1][S:2]([C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)=[C:7]([N+:20]([O-])=O)[CH:6]=1)(=[O:4])=[O:3].C(O)(=O)C.[H][H]>[Pd].[OH-].[Na+]>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[Cl:16])[O:9][C:8]1[CH:18]=[CH:19][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][C:7]=1[NH2:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A slurry of 10.5 g (0.0290 mole) of 4-(4-(methylsulfonyl)-2-nitrophenoxy)-1,2-dichlorobenzene and 350 ml of glacial acetic acid was placed in a Parr bottle and 0.5 g of 5% palladium on carbon added under nitrogen. The mixture was placed on a Parr hydrogenator apparatus and the desired reduction carried out with 50 pounds per square inch (psi) of hydrogen. Two batches of equal size were run and the catalyst removed by filtration. The solvent was removed in vacuo leaving crude product which was slurried in aqueous NaOH to remove any residual acetic acid. The aqueous layer was decanted from the product which was dried, to obtain 14.4 g (74.8% yield) of product. Recrystallization from ethanol and water afforded purified 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)benzenamine, mp 119°-121° C.
Workup
- additionadded under nitrogen
- customthe catalyst removed by filtration
- customThe solvent was removed in vacuo
- customleaving crude product which
- customto remove any residual acetic acid
- customThe aqueous layer was decanted from the product which
- customwas dried
Sources & evidence
- ORD record
- ord-0c3b752191a04f23a9762a4f6c5c83f6
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04349568
Reaction notes
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