Hydrochloric Acid → HCID 12822521, compound

HRID 1647782Notes

Reaction equation

HRID 1647782 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-])=O.Cl>O.C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 12822520N-(4-nitrobenzyl)methanesulfonamide

Product 1

HCID 12822521HCID 12822521, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 25.9 g (113 mmol, 1.0 equiv.) of N-[(4-nitrophenyl)methyl]methanesulfonamide in 113 mL of 1N HCl (113 mmol, 1.0 equiv.), 113 mL of water and 225 mL of ethanol was added 5.18 g of 10% palladium on carbon. This mixture was hydrogenated in a Parr apparatus at 60 psi for sixteen hours. The mixture was filtered through Celite. The ethanol was removed in vacuo and the pH adjusted to 9, at which point the product had precipitated. The precipitate was isolated by filtration and dried in vacuo to yield 18.0 g (80%) of N-[(4-aminophenyl)methyl]-methanesulfonamide.

Workup

  1. waitThis mixture was hydrogenated in a Parr apparatus at 60 psi for sixteen hours
  2. filtrationThe mixture was filtered through Celite
  3. customThe ethanol was removed in vacuo
  4. customhad precipitated
  5. customThe precipitate was isolated by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-eea9a106f1014941a0cb383eee713e6d
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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