Ammonium Chloride → HCID 15870498, compound

HRID 378298Notes

Reaction equation

HRID 378298 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)C)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[C:6]([NH2:8])[CH:7]=1.[Cl-].[NH4+]>[OH-].[Na+]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([S:10]([NH:9][C:4]2[CH:5]=[C:6]([NH2:8])[CH:7]=[C:2]([NH2:1])[CH:3]=2)(=[O:12])=[O:11])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 15870497HCID 15870497, compound

Product 1

HCID 15870498HCID 15870498, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.105 g (0.00033 mol) of N-[4-(3,5-diamino-phenylsulfamoyl)-phenyl]-acetamide was dissolved in 6.5 ml of 1N NaOH and boiled at reflux for 15 hours. The reaction mixture was treated with 50 ml of saturated ammonium chloride solution and extracted twice with 100 ml of ethyl acetate each time. The combined organic phases were washed with saturated sodium chloride solution and dried over MgSO4. After removal of the solvent the residue was chromatographed on aluminium oxide (neutral, activity 1), firstly with 5% and then 10% methanol in dichloromethane. There was obtained 0.05 g (55%) of 4-amino-N-(3,5-diamino-phenyl)benzenesulfonamide as a beige solid; m.p.: 188-190° C.

Workup

  1. temperatureat reflux for 15 hours
  2. extractionextracted twice with 100 ml of ethyl acetate each time
  3. washThe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent the residue
  6. customwas chromatographed on aluminium oxide (neutral, activity 1), firstly with 5%

Sources & evidence

ORD record
ord-b4df4ff0a50f418c91678bbe90b1dbe0
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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