Water → [2-(4-Formyl-2-methoxy-3-nitrophenoxy)ethyl]propane-1-sulfonamide

HRID 1821437Notes

Reaction equation

HRID 1821437 reaction equation
CO[CH:3]([O:19]C)[C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10]N)=[C:6]([O:14][CH3:15])[C:5]=1[N+:16]([O-:18])=[O:17].C([N:23](CC)CC)C.[CH2:28]([S:31](Cl)(=[O:33])=[O:32])[CH2:29][CH3:30].O>C1COCC1>[CH:3]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][CH:28]([S:31]([NH2:23])(=[O:33])=[O:32])[CH2:29][CH3:30])=[C:6]([O:14][CH3:15])[C:5]=1[N+:16]([O-:18])=[O:17])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 689994632-(4-Dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamine

Product 1

HCID 86628224[2-(4-Formyl-2-methoxy-3-nitrophenoxy)ethyl]propane-1-sulfonamideYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamine (0.5 g, 1.8 mmol) obtained in Step 3 in THF (10 mL) was added with triethylamine (0.38 mL, 2.7 mmol) and n-propanesulfonyl chloride (0.24 mL, 2.2 mmol), followed by stirring at room temperature for 3 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was added with methanol (6.0 mL) and 1 mol/L hydrochloric acid, followed by stirring for 15 minutes. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain [2-(4-formyl-2-methoxy-3-nitrophenoxy)ethyl]propane-1-sulfonamide (0.39 g, 62%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was added with methanol (6.0 mL) and 1 mol/L hydrochloric acid
  6. stirringby stirring for 15 minutes
  7. additionThe reaction mixture was added with water
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aada1a53d84d4e73a5821c2af168b354
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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