Stannous Chloride → 3-amino-N,N-dimethylbenzene-1-sulfonamide

HRID 1633919

Reaction equation

HRID 1633919 reaction equation
[CH3:1][N:2]([CH3:15])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)(=[O:5])=[O:4].Cl[Sn]Cl>C(O)C>[NH2:12][C:8]1[CH:7]=[C:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 224495N,N-Dimethyl 3-nitrobenzenesulfonamide

Product 1

HCID 2355203-amino-N,N-dimethylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the above N,N-dimethyl-3-nitro-benzenesulfonamide (20.4 mmol, 4.7 g) in ethanol (50 mL) was added SnCl2 (105 mmol, 19.9 g) and the mixture was refluxed for 1 hour. Upon cooling, the solvent was removed in vacuo. Ethyl acetate (200 mL) and NaHCO3 (sat, 100 mL) were added to the residue followed by another 200 mL ethyl acetate and 500 mL water. The phases were separated and the organic phase was washed twice with water. The organic phase was filtered, washed with water (2×100 mL) dried over MgSO4 and evaporated to leave the title compound.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureUpon cooling
  3. customthe solvent was removed in vacuo
  4. additionEthyl acetate (200 mL) and NaHCO3 (sat, 100 mL) were added to the residue
  5. customThe phases were separated
  6. washthe organic phase was washed twice with water
  7. filtrationThe organic phase was filtered
  8. washwashed with water (2×100 mL)
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-fb1a7a7b4f2a44908246eed1685ac2a6
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Linked notes

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