Ammonium Chloride → 2-Amino-5-(benzyloxy)benzenesulfonamide

HRID 601278Notes

Reaction equation

HRID 601278 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:19]([O-])=O)=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.O.[Fe]>[NH2:19][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]=1[S:15]([NH2:18])(=[O:16])=[O:17]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 670638975-(Benzyloxy)-2-nitrobenzenesulfonamide

Product 1

HCID 670639862-Amino-5-(benzyloxy)benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product of Example 304C (3.85 g, 0.0125 mol) was treated with iron powder (4.3 g, 0.077 mol, 6.15 equivalent) and ammonium chloride (4.4 g, 0.082 mol) in methanol (100 mL) and water (50 mL), and stirred at reflux for 1 hour. The hot reaction mixture was filtered through fluted filter paper and washed with hot methanol. The filtrate was concentrated under reduced pressure to a white semi-solid that was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to give the title compound as a off white solid (2.5 g). 1H NMR (300 MHz, DMSO-d6) δ ppm 4.98 (s, 2 H) 5.46 (s, 2 H) 6.76 (d, J=8.82 Hz, 1 H) 7.01 (dd, J=8.82, 2.94 Hz, 1 H) 7.21 (d, J=2.94 Hz, 1 H) 7.23 (s, 2 H) 7.37 (m, 5 H). ESI m/z (M+H)+279. ESI m/z (M−H)−277.

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationThe hot reaction mixture was filtered
  3. filtrationthrough fluted filter paper
  4. washwashed with hot methanol
  5. concentrationThe filtrate was concentrated under reduced pressure to a white semi-solid
  6. customthat was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bd108c055e4542cda1711173d60a4a37
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

Loading…