Sodium Hydroxide → 2-Amino-5-methoxybenzenesulfonamide

HRID 730484Notes

Reaction equation

HRID 730484 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-ec0b28ef7da14e61b1cbec6381f5e1b6
Source dataset
uspto-grants-2009_09
Patent number
US07582754B2

Reaction notes

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