Sodium Hydroxide → 2-Amino-5-methoxybenzenesulfonamide

HRID 1176989Notes

Reaction equation

HRID 1176989 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[NH:7]C(=O)[NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:7][C:6]1[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[S:10]([NH2:9])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 125284907-Methoxy-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 112526652-Amino-5-methoxybenzenesulfonamideYield 61%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 7-methoxy-1,1-dioxo-1,4-dihydro-2H-1λ6-benzo[1,2,4]thiadiazin-3-one (Example 2a, 15 g, 65.7 mmol) in a 50% aqueous sulfuric acid solution (140 mL) was heated at 130° C. for 6 h. The solution was then poured over ice and neutralized at 0° C. with the addition of saturated aqueous sodium hydroxide solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with brine, and dried over magnesium sulfate, filtered and dried in vacuo to afford the desired product, 2-amino-5-methoxy-benzenesulfonamide (8.1 g, 40.1 mmol, 61% yield) as a brown solid. See procedure described in Girard, Y., et al., J. Chem. Soc. Perkin Trans 1, 1043-1047 (1979). 1H NMR (400 MHz, DMSO -d6): δ 3.65 (s, 3H), 5.40 (s, 2H), 6.73 (d, 1H, J=8.8 Hz), 6.90 (dd, 1H, J1=8.8 Hz, J2=2.8 Hz), 7.07 (d, 1H, J=2.8 Hz), 7.19 (s, 2H).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-353cdab22631473c828fcdc88a2b1ae5
Source dataset
uspto-grants-2010_11
Patent number
US07842838B2

Reaction notes

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