Hydrochloric Acid → SULFONILAMIDE,N-(4-INDOLYL)

HRID 1585727Notes

Reaction equation

HRID 1585727 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl>[OH-].[Na+]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19601792HCID 19601792, compound

Product 1

HCID 10637020SULFONILAMIDE,N-(4-INDOLYL)Yield 66%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.15 g (0.00045 mol) of N-[4-(1H-indol-4-ylsulfamoyl)-phenyl]-acetamide was dissolved in 4 ml of 1N NaOH and boiled at reflux for 1 hour. After cooling the mixture was adjusted to pH 6 with 0.1N HCl and the precipitate which separated was filtered off. The material on the suction filter was washed with copious water and dried. It was subsequently chromatographed on silica gel with ethyl acetate/hexane 1:1. There was obtained 0.085 g (66%) of 4-amino-N-(1H-indol-4-yl)-benzenesulfonamide as a white amorphous solid; m.p.: 215° C.

Workup

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

Sources & evidence

ORD record
ord-502d2b029ad4439982fcb9f90ae19e4a
Source dataset
uspto-grants-1999_08
Patent number
US05939451

Reaction notes

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