Ethylenediamine → 4-(N,S-Dimethylsulfonimidoyl)benzylamine

HRID 527377Notes

Reaction equation

HRID 527377 reaction equation
[CH3:1][N:2]=[S:3]([C:6]1[CH:23]=[CH:22][C:9]([CH2:10][N:11]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:8][CH:7]=1)([CH3:5])=[O:4].NCCN.C(#N)C.O1CCCC1>C(O)C>[CH3:1][N:2]=[S:3]([C:6]1[CH:23]=[CH:22][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1)([CH3:5])=[O:4]

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 867116422-(4-(N,S-Dimethylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Product 1

HCID 867116434-(N,S-Dimethylsulfonimidoyl)benzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-(N,S-dimethylsulfonimidoyl)benzyl)isoindoline-1,3-dione (189 mg, 0.58 mmol) and 1,2-diaminoethane (132 μL, 3.44 mmol) in a 2:1:1 mixture of acetonitrile, tetrahydrofuran and ethanol (2 mL) is heated at reflux for 1 h. All volatiles are removed under reduced pressure, and the residue is treated with dichloromethane. The mixture is filtered, and the filtrate is concentrated under reduced pressure. Yield: 114 mg (85% of theory); ESI mass spectrum: [M+H]+=199; r.t. HPLC: 0.22 min (X011_S03).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 h
  3. customAll volatiles are removed under reduced pressure
  4. additionthe residue is treated with dichloromethane
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customr.t
  8. custom0.22 min (X011_S03)

Sources & evidence

ORD record
ord-e79c3980c4ee481c8d121f645d85ca49
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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