Sodium Carbonate → 4-amino-N-butylbenzenesulfonamide

HRID 1633909Notes

Reaction equation

HRID 1633909 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:15]([NH:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:16][CH2:17][CH3:18]>O.CO>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 1577957N-butyl-4-nitrobenzenesulfonamide

Product 1

HCID 2894604-amino-N-butylbenzenesulfonamideYield 6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sodium dithionite (11.4 g, 65 mmol) and sodium carbonate (5.6 g, 53 mmol) were dissolved in water (65 mL) and heated to 70° C. A suspension of the above 4-nitrophenylsulfonamide (2.64 g, 10.2 mmol) in methanol (65 mL) was added and the resulting mixture was stirred at 70° C. for 1.5 hour. The cooled mixture was filtered and the volume of the filtrate was reduced by 50% in vacuo. The aqueous mixture was extracted with ethyl acetate (3×60 mL), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford 0.14 g (6%) of 4-amino-N-butylbenzenesulfonamide as a solid.

Workup

  1. additionwas added
  2. filtrationThe cooled mixture was filtered
  3. extractionThe aqueous mixture was extracted with ethyl acetate (3×60 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-493fdc680ca1478198308817d01ced0e
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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