Hydrochloric Acid → 3-Amino-N,N-diethylbenzene-1-sulfonamide

HRID 1110673Notes

Reaction equation

HRID 1110673 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)(=[O:6])=[O:5])[CH3:2].Cl>CO>[CH2:16]([N:3]([CH2:1][CH3:2])[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)(=[O:6])=[O:5])[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 232031N,N-Diethyl-3-nitrobenzenesulfonamide

Product 1

HCID 29635153-Amino-N,N-diethylbenzene-1-sulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The N,N-diethyl-3-(nitro)benzenesulfonamide (3.9 g) was dissolved in methanol (60 ml) and, after an addition of conc. hydrochloric acid (10 ml), reduced iron (4.2 g) was added and the mixture was stirred at room temperature for 2 hours. After filtration, methanol was evaporated under a reduced pressure and the residue was made basic with an addition of 4N sodium hydroxide. The iron oxide precipitated was separated by filtration, washed with methylene chloride (50 ml). Also the filtrate was extracted with methylene (50 ml×2) and combined with the methylene chloride washing, followed by drying over anhydrous sodium sulfate. Evaporation of the solvent gave N,N-diethyl-3-(amino)benzenesulfonamide (3.0 g) (m.p. 82°-84° C.).

Workup

  1. additionwas added
  2. filtrationAfter filtration, methanol
  3. customwas evaporated under a reduced pressure
  4. additionthe residue was made basic with an addition of 4N sodium hydroxide
  5. customThe iron oxide precipitated
  6. customwas separated by filtration
  7. washwashed with methylene chloride (50 ml)
  8. extractionAlso the filtrate was extracted with methylene (50 ml×2)
  9. dry with materialby drying over anhydrous sodium sulfate
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5f51a9bab7004a12956b43190044f6f3
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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