Methylamine → HCID 53711596, compound

HRID 2290187Notes

Reaction equation

HRID 2290187 reaction equation
[CH:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=[O:2].[CH2:16]([N:18](CC)CC)C.CN>C(Cl)(Cl)Cl>[CH3:16][NH:18][S:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:3]([CH:1]=[O:2])[CH2:4][CH2:5]2)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 104219941-formyl-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 53711596HCID 53711596, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 31.07 g (0.126 mol) of N-formyl-5-chlorosulfonylindoline in 400 ml of ice-cold methylene chloride was added 37 ml (0.252 mol) of triethylamine and 30 ml (0.252 mol) of 40% aqueous methylamine solution, portionwise over twenty minutes. The mixture was allowed to warm to room temperature and then heated to reflux in an oil bath for one hour while stirred mechanically. Thin layer chromatography with chloroform showed the reaction was complete. The aqueous layer was removed. The methylene chloride layer was washed with water and dried over sodium sulfate. The solution was concentrated under reduced pressure and the residue allowed to air dry to give 23.74 g (0.0988 mol) (75% by weight yield) of 5-methylsulfamoyl-N-formylindoline.

Workup

  1. waitportionwise over twenty minutes
  2. temperatureheated
  3. temperatureto reflux in an oil bath for one hour
  4. customThe aqueous layer was removed
  5. washThe methylene chloride layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. customto air dry

Sources & evidence

ORD record
ord-56042bb7a0354d549e2a8c9839422690
Source dataset
uspto-grants-1986_10
Patent number
US04615966

Reaction notes

Loading…