N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenesulfonamide → 2-amino-N-(3-(dimethylamino)propyl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide

HRID 1042668Notes

Reaction equation

HRID 1042668 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][N:6]([CH3:23])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-])=O)(=[O:9])=[O:8]>CCO.[Pd]>[NH2:20][C:11]1[CH:12]=[C:13]([C:16]([F:18])([F:17])[F:19])[CH:14]=[CH:15][C:10]=1[S:7]([N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:24])[CH3:23])(=[O:8])=[O:9]

Participants

4

Reactant 1

HCID 59427951N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenesulfonamide

Product 1

HCID 594280112-amino-N-(3-(dimethylamino)propyl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an argon purged solution of N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenesulfonamide (255 mg, 0.69 mmol) in EtOH (10 ml) was added Pd/C (73 mg, 0.069 mmol, 10%). The reaction mixture was placed under an atmosphere of H2 gas and allowed to stir for 2 h. The reaction mixture was purged with argon and filtered through Celite. The reaction was washed with EtOH (10 ml) and concentrated under reduced pressure to afford 2-amino-N-(3-(dimethylamino)propyl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide as a dark oil. MS m/z=340.1 [M+H]+. Calc'd for C13H20P3N3O2S: 339.4.

Workup

  1. customThe reaction mixture was purged with argon
  2. filtrationfiltered through Celite
  3. washThe reaction was washed with EtOH (10 ml)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e28725aa4c1437c80f22f477455becf
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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