Ammonium Chloride → 4-amino-N-isopropylbenzenesulfonamide

HRID 2407988Notes

Reaction equation

HRID 2407988 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[Cl-].[NH4+]>O.[Fe]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([S:5]([NH:4][CH:1]([CH3:3])[CH3:2])(=[O:7])=[O:6])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 2054536N-Isopropyl-4-nitrobenzenesulfonamide

Product 1

HCID 8336664-amino-N-isopropylbenzenesulfonamideYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of N-isopropyl-4-nitro-benzenesulfonamide (9.0 g, 37.0 mmol) ethanol (500 mL) was added iron powder (11.0 g, 196.0 mmol) and the solution of ammonium chloride (22.0 g, 392.0 mmol) in water (150 mL). After the reaction mixture was refluxed for 3 h, the iron was filtered off and the filtrate was basified to pH 9 by addition of sodium carbonate. The reaction mixture was extracted with ethyl acetate (300 mL×2). The extract was washed with water (130 mL×2) and brine (130 mL×2), dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 20-60% ethyl acetate in petroleum ether) to afford 4-amino-N-isopropyl-benzenesulfonamide (7.0 g, 89%) as a yellow powder: MS (ESI) M+1=215.

Workup

  1. temperatureAfter the reaction mixture was refluxed for 3 h
  2. filtrationthe iron was filtered off
  3. additionthe filtrate was basified to pH 9 by addition of sodium carbonate
  4. extractionThe reaction mixture was extracted with ethyl acetate (300 mL×2)
  5. washThe extract was washed with water (130 mL×2) and brine (130 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 20-60% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6d7cf0a59983433a9580c2a6184ae20f
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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