Ammonium Chloride → 2-amino-4-methoxy-N-(4-chlorophenyl)-benzenesulfonamide

HRID 477876Notes

Reaction equation

HRID 477876 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[C:5]([N+:20]([O-])=O)[CH:4]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:20][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 9546834-methoxy-2-nitro-N-(4-chlorophenyl)benzenesulfonamide

Product 1

HCID 198725182-amino-4-methoxy-N-(4-chlorophenyl)-benzenesulfonamideYield 75.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-methoxy-2-nitro-N-(4-chlorophenyl)benzenesulfonamide (37.2 g) and ammonium chloride (75.4 g) in a mixture of methanol (400 ml) and water (400 ml) was added iron (76.4 g) in small portions over a period of one and half hours at 100° C. The reaction mixture was refluxed for 8 hours and the hot mixture was filtrated. The filtrated cake was washed with hot methanol. The combined filtrates were evaporated under reduced pressure and the residue was extracted three times with ethyl acetate. The extracts were washed with water, dried, and concentrated to give crude product, which was purified by silica gel column-chromatography (elution by methylene chloride) to yield 2-amino-4-methoxy-N-(4-chlorophenyl) benzenesulfonamide (25.77 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. filtrationthe hot mixture was filtrated
  3. washThe filtrated cake was washed with hot methanol
  4. customThe combined filtrates were evaporated under reduced pressure
  5. extractionthe residue was extracted three times with ethyl acetate
  6. washThe extracts were washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto give crude product, which
  10. customwas purified by silica gel column-chromatography (elution by methylene chloride)

Sources & evidence

ORD record
ord-9fc2df101d4c47f08b75e80b09a58621
Source dataset
uspto-grants-1989_12
Patent number
US04889851

Reaction notes

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