N-(1,1,3-trioxo-1,2,3,4-tetrahydro-1lambda6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide → 2-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

HRID 730489Notes

Reaction equation

HRID 730489 reaction equation
[O:1]=[S:2]1(=[O:18])[C:7]2[CH:8]=[C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:11][C:6]=2[NH:5]C(=O)[NH:3]1>Cl.O>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])=[CH:8][C:7]=1[S:2]([NH2:3])(=[O:1])=[O:18]

Participants

4

Reactant 1

HCID 24858396N-(1,1,3-trioxo-1,2,3,4-tetrahydro-1lambda6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide

Product 1

HCID 249506572-Amino-5-[(methylsulfonyl)amino]benzenesulfonamideYield 45.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

N-(1,1,3-Trioxo-1,2,3,4-tetrahydro-1λ6-benzo[1,2,4]thiadiazin-7-yl)-methanesulfonamide (Example 3c, 1 g, 3.4 mmol) was suspended in 12 M aqueous hydrochloric acid solution (60 mL). The mixture was stirred at 105° C. for 16 h. All solids were dissolved at this point. The mixture was diluted with water (250 mL). The solution was concentrated in vacuo to an orange solid. The solid was dissolved in water (20 mL) and concentrated in vacuo to an orange solid. The solid was dissolved in water (5 mL) and the product was extracted into ethyl acetate (6×20 mL). The combined organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to an orange solid. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm, 75% ethyl acetate in hexanes) afforded the desired product, 2-amino-5-methanesulfonylamino-benzenesulfonamide (0.41 g, 1.55 mmol, 45% yield), as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 2.86 (3H, s), 5.77 (2H, s), 6.76 (1H, d, J=8.6 Hz), 7.11 (1H, dd, J1=8.6 Hz, J2=2.4 Hz), 7.25 (2H, bs), 7.43 (1H, d, J=3.1 Hz), 9.16 (1H, s).

Workup

  1. dissolutionAll solids were dissolved at this point
  2. concentrationThe solution was concentrated in vacuo to an orange solid
  3. dissolutionThe solid was dissolved in water (20 mL)
  4. concentrationconcentrated in vacuo to an orange solid
  5. dissolutionThe solid was dissolved in water (5 mL)
  6. extractionthe product was extracted into ethyl acetate (6×20 mL)
  7. dry with materialThe combined organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to an orange solid
  10. customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm, 75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c0a50daa4a034035bd767df14f0586db
Source dataset
uspto-grants-2009_09
Patent number
US07582754B2

Reaction notes

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