3-Cyanobenzene-1-sulfonyl chloride → 3-(Aminomethyl)-N,N-dimethylbenzenesulfonamide

HRID 447808Notes

Reaction equation

HRID 447808 reaction equation
CO.[CH3:3][NH:4][CH3:5].[C:6]([C:8]1[CH:9]=[C:10]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1)#[N:7]>>[NH2:7][CH2:6][C:8]1[CH:9]=[C:10]([S:14]([N:4]([CH3:5])[CH3:3])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 22497844Dimethylamine methanol

Product 1

HCID 167953563-(Aminomethyl)-N,N-dimethylbenzenesulfonamide

Procedure

(Step 1) To a 2M dimethylamine methanol solution (3.7 ml) was added 3-cyanobenzenesulfonyl chloride (1.5 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, saturated brine was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. 10% Palladium carbon powder (0.79 g) was added to a solution (10 ml) of the residue in ethanol, and the mixture was stirred overnight under a hydrogen atmosphere (1 atm). The solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give 3-(aminomethyl)-N,N-dimethylbenzenesulfonamide (1.0 g) as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure, saturated brine
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe solvent was evaporated under reduced pressure
  5. addition10% Palladium carbon powder (0.79 g) was added to a solution (10 ml) of the residue in ethanol
  6. stirringthe mixture was stirred overnight under a hydrogen atmosphere (1 atm)
  7. filtrationThe solution was filtered through celite
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ffd61581c985468da23315df0359213d
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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