Ammonium Hydroxide → 4-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

HRID 1514859Notes

Reaction equation

HRID 1514859 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[NH4+:23].[OH-]>O1CCOCC1.O>[NH2:23][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 47954984-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

Product 1

HCID 669661164-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of 4-chloro-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide (0.22 g) in dioxane (2 mL) was added NH4OH (3 mL). The reaction mixture was heated to 95° C. for 8 h. The mixture was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The extract was dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 hexane/EtOAc) afforded 4-amino-N-(3,4-dimethyl-phenyl)-3-nitro-benzenesulfonamide.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 3:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-b777f18b188341a190f700d440237782
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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