Hydrochloric Acid → N-methyl-2,3-dihydro-1H-indole-5-sulfonamide

HRID 2290188Notes

Reaction equation

HRID 2290188 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](C=O)[CH2:10][CH2:9]2)(=[O:5])=[O:4].Cl>CO.C(Cl)(Cl)Cl>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53711596HCID 53711596, compound

Product 1

HCID 6502484N-methyl-2,3-dihydro-1H-indole-5-sulfonamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 23.42 g (0.0975 mol) of 5-methylsulfamoyl-N-formylindoline in 500 ml of methanol was added 40 ml of concentrated hydrochloric acid. The solution was heated to reflux for one hour. Thin layer chromatography in chloroform showed the reaction was complete. The solution was allowed to cool, and then the methanol was removed under reduced pressure. The aqueous slurry remaining was dissolved ice water and neutralized by the addition of sodium hydroxide solution. The precipitate was extracted with methylene chloride, washed with water and saturated aqueous sodium chloride solution. The solution was dried over sodium sulfate and then concentrated under reduced pressure. The residue was allowed to air dry to give 17.02 g (0.08 mol) (82% by weight yield) of 5-methylsulfamoylindoline.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for one hour
  3. temperatureto cool
  4. customthe methanol was removed under reduced pressure
  5. dissolutionThe aqueous slurry remaining was dissolved ice water
  6. additionneutralized by the addition of sodium hydroxide solution
  7. extractionThe precipitate was extracted with methylene chloride
  8. washwashed with water and saturated aqueous sodium chloride solution
  9. dry with materialThe solution was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto air dry

Sources & evidence

ORD record
ord-541658c630524170b4e7bf9f9854ef2e
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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