Chloroform → 5-bromo-6-(methylsulfamoyl)-N-acetylindoline

HRID 2290183Notes

Reaction equation

HRID 2290183 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](Cl)(=[O:13])=[O:12])[N:7]([C:15](=[O:17])[CH3:16])[CH2:6][CH2:5]2.CN.[CH2:20]([N:22](CC)CC)C.C(Cl)(Cl)Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[S:11](=[O:13])(=[O:12])[NH:22][CH3:20])[N:7]([C:15](=[O:17])[CH3:16])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6329MethylamineHCID 8471TriethylamineHCID 140245841-acetyl-5-bromo-2,3-dihydro-1H-indole-6-sulfonyl chloride

Product 1

HCID 140245855-bromo-6-(methylsulfamoyl)-N-acetylindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-bromo-6-chlorosulfonyl-N-acetylindoline, 71.83 g (0.212 mol) in tetrahydrofuran was added a 40% aqueous solution of 2 equivalents of methylamine and 2 equivalents of triethylamine. The mixture was heated to reflux for 1.5 hours, then allowed to cool. Thin layer chromatography with chloroform showed that the reaction was complete. The cooled mixture was evaporated under reduced pressure, and the resulting white solid was suppended in hot methanol, filtered and washed with methanol and allowed to dry overnight. 65.12 g of 5-bromo-6-methylsulfamoyl-N-acetylindoline was obtained (92% by weight yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. customThe cooled mixture was evaporated under reduced pressure
  5. filtrationfiltered
  6. washwashed with methanol
  7. customto dry overnight

Sources & evidence

ORD record
ord-74cce179f5f642b2867624aa9b45c43c
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

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