Hydrochloric Acid → 4-amino-N-(2,6-dibromo-pyridin-4-yl)-benzenesulfonamide

HRID 610830Notes

Reaction equation

HRID 610830 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[C:4]([Br:22])[N:3]=1.Cl>[OH-].[Na+]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[CH:7]=[C:2]([Br:1])[N:3]=[C:4]([Br:22])[CH:5]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10623382N-[4-(2,6-dibromo-pyridin-4-ylsulfamoyl)-phenyl]-acetamide

Product 1

HCID 108113474-amino-N-(2,6-dibromo-pyridin-4-yl)-benzenesulfonamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

6.2 g (0.0138 mol) of N-[4-(2,6-dibromo-pyridin-4-yl-sulfamoyl)-phenyl]-acetamide were dissolved in 138 ml of 1N NaOH and boiled at reflux for 2 hours. After cooling the mixture was adjusted to pH 6 with 2N HCl and the precipitate which separated was filtered off. The material on the suction filter was washed well with water and dried. It was subsequently chromatographed on silica gel with ethyl acetate/hexane 1:2→1:1. There were obtained 4.86 g (86%) of 4-amino-N-(2,6-dibromo-pyridin-4-yl)-benzenesulfonamide as beige crystals; m.p.: 220-222° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureAfter cooling the mixture
  3. customthe precipitate which separated
  4. filtrationwas filtered off
  5. filtrationThe material on the suction filter
  6. washwas washed well with water
  7. customdried
  8. customIt was subsequently chromatographed on silica gel with ethyl acetate/hexane 1:2→1:1

Sources & evidence

ORD record
ord-4b72e52c7cc140faa8dc7f38e0533207
Source dataset
uspto-grants-1999_12
Patent number
US05998665

Reaction notes

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