HCID 22007168, compound → 3-(2-Amino-1-hydroxyethyl)-4-methoxybenzene-1-sulfonamide

HRID 323788Notes

Reaction equation

HRID 323788 reaction equation
[N:1]([CH2:4][CH:5]([C:7]1[CH:12]=[C:11]([S:13](=[O:16])(=[O:15])[NH2:14])[CH:10]=[CH:9][C:8]=1[O:17][CH3:18])[OH:6])=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][CH:5]([C:7]1[CH:12]=[C:11]([S:13](=[O:15])(=[O:16])[NH2:14])[CH:10]=[CH:9][C:8]=1[O:17][CH3:18])[OH:6]

Participants

4

Reactant 1

HCID 22007168HCID 22007168, compound

Product 1

HCID 99060413-(2-Amino-1-hydroxyethyl)-4-methoxybenzene-1-sulfonamideYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

11 g (0.040 mol) of (−)-α-azidomethyl-2-methoxy-5-sulphamoylbenzenemethanol, 500 ml of ethanol and 2.2 g of 10% palladium on charcoal are introduced into a 1-liter reactor. The reactor is closed and purged with nitrogen, and the mixture is stirred under 400 kPa of hydrogen at room temperature for 3 hours. The reaction mixture is then filtered through Whatman paper, the recovered catalyst is suspended in 200 ml of methanol and the mixture is heated to boiling for 30 minutes. It is then filtered through Whatman paper, the filtrates are combined and concentrated and the residue is dried in a desiccator under vacuum over phosphorus pentoxide. 9.4 g of (−)-α-aminomethyl-2-methoxy-5-sulphamoylbenzenemethanol are obtained.

Workup

  1. customThe reactor is closed
  2. custompurged with nitrogen
  3. filtrationThe reaction mixture is then filtered through Whatman paper
  4. temperaturethe mixture is heated
  5. waitto boiling for 30 minutes
  6. filtrationIt is then filtered through Whatman paper
  7. concentrationconcentrated
  8. dry with materialthe residue is dried in a desiccator under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-206430ca2e52421a9497c3df1bcb391f
Source dataset
uspto-grants-2001_04
Patent number
US06214882B1

Reaction notes

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