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

HRID 494445Notes

Reaction equation

HRID 494445 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)benzenesulfonamideYield 97.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of the product of Example 2C (7.26 g, 23.57 mmol), ammonium chloride (8.27 g, 155 mmol), and iron powder (8.11 g, 145 mmol) in methanol (188 mL) and water (94 mL) was stirred at reflux for 2 hours. The mixture was filtered while hot through Celite®, and the filter cake was washed with hot methanol (200 mL). The filtrate was concentrated to an approximate volume of 100 mL and then extracted with ethyl acetate (400 mL). The organic layer was washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered through Celite® and concentrated in vacuo to afford the title compound (6.37 g, 97%). 1H NMR (300 MHz, DMSO-d6): δ 7.38 (m, 7 H), 7.22 (m, 2 H), 7.01 (dd, J=8.82, 2.94 Hz, 1 H), 6.76 (d, J=8.82 Hz, 1 H), 5.46 (s, 2 H), 4.98 (s, 2 H).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe mixture was filtered while hot through Celite®
  3. washthe filter cake was washed with hot methanol (200 mL)
  4. concentrationThe filtrate was concentrated to an approximate volume of 100 mL
  5. extractionextracted with ethyl acetate (400 mL)
  6. washThe organic layer was washed with water and saturated sodium chloride solution
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered through Celite®
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3ab4b57e56c4e99a9b3e7a7ff10e503
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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