Ammonium Hydroxide → 2-Methoxy-4-nitrobenzenesulfonamide

HRID 912567Notes

Reaction equation

HRID 912567 reaction equation
[OH-].[NH4+:2].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[S:14](Cl)(=[O:16])=[O:15]>[NH4+].[Cl-]>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[S:14]([NH2:2])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 3094582-Methoxy-4-nitrobenzenesulfonyl chloride

Product 1

HCID 203309102-Methoxy-4-nitrobenzenesulfonamideYield 68.9%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a concentrated solution of ammonium hydroxide (28%, 2.5 mL, 20 mmol) was added cautiously 2-methoxy-4-nitrobenzenesulfonyl chloride (0.25 g, 1.0 mmol). After stirring 24h the reaction mixture was added to satd NH4Cl (50 mL) and extracted with DCM (2×50 mL). The combined extracts were washed with brine, dried (anhyd Na2SO4) and concentrated under reduced pressure. The crude residue was chromatographed (silica, MeOH/DCM, 0:100 to 10:90) to yield 2-methoxy-4-nitrobenzenesulfonamide (0.16 g, 68%) as a pale brown solid. 1H-NMR (DMSO-d6) δ 7.99 (1H, d), 7.90-7.95 (2H, m), 7.47 (2H, br s), 4.04 (3H, s).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (anhyd Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was chromatographed (silica, MeOH/DCM, 0:100 to 10:90)

Sources & evidence

ORD record
ord-e46f01c0d6c447ec9f0db80ddd26adba
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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