Potassium Hydroxide → HCID 4685957, compound

HRID 1836611Notes

Reaction equation

HRID 1836611 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])(=[O:12])=[O:11])([O-])=O.O.O.Cl[Sn]Cl.[OH-].[K+]>CCOC(C)=O>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 779183Benzenesulfonamide, N-(2,5-dimethylphenyl)-2-nitro-

Product 1

HCID 4685957HCID 4685957, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-nitro-N-(2,5-dimethyl-phenyl)-benzenesulfonamide (6.1 g, 20 mmol) in EtOAc (60 mL) is treated with SnCl2.2H2O (22.5 g, 100 mmol). The reaction mixture is heated to reflux for 30 minutes and then allowed to cool to room temperature. 2 N KOH (250 mL, 500 mmol) is added and the resulting mixture stirred vigorously until all solids dissolve. The aqueous layer is separated and extracted 2×100 mL EtOAc. The combined organic layers are washed with sat. brine, dried over MgSO4, filtered, and concentrated to a solid, which is recrystallized from hot EtOAc/hexanes to provide 2-amino-N-(2,5-dimethyl-phenyl)-benzenesulfonamide.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 30 minutes
  3. dissolutiondissolve
  4. customThe aqueous layer is separated
  5. extractionextracted 2×100 mL EtOAc
  6. washThe combined organic layers are washed with sat. brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to a solid, which
  10. customis recrystallized from hot EtOAc/hexanes

Sources & evidence

ORD record
ord-0824feb0d4a54ccb8069ca13a12d9c0f
Source dataset
uspto-grants-2004_08
Patent number
US06777446B2

Reaction notes

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