Hydrochloric Acid → 5-Bromo-6-methylsulfamoylindoline

HRID 2290184Notes

Reaction equation

HRID 2290184 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](=[O:15])(=[O:14])[NH:12][CH3:13])[N:7](C(=O)C)[CH2:6][CH2:5]2.Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](=[O:15])(=[O:14])[NH:12][CH3:13])[NH:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 140245855-bromo-6-(methylsulfamoyl)-N-acetylindoline

Product 1

HCID 140245865-Bromo-6-methylsulfamoylindolineYield 98.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 65.11 g (0.195 mol) of 5-bromo-6-methylsulfamoyl-N-acetylindoline in 200 ml dioxane was added 146 ml (1.75 mol) concentrated hydrochloric acid. The mixture was stirred and refluxed for 1.5 hours and allowed to cool. The mixture was then concentrated under reduced pressure, cooled in an ice bath and neutralized with 10% sodium hydroxide solution to pH 7. The resulting white precipitate was filtered, washed several times with water and allowed to dry overnight to give 55.92 g (98% by weight yield) of 5-bromo-6-methylsulfamoylindoline.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. temperatureto cool
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. temperaturecooled in an ice bath
  5. filtrationThe resulting white precipitate was filtered
  6. washwashed several times with water
  7. customto dry overnight

Sources & evidence

ORD record
ord-8ae3709c973d43608632bfc90d5e3e98
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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