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

HRID 527377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527377
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 867116434-(N,S-Dimethylsulfonimidoyl)benzylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e79c3980c4ee481c8d121f645d85ca49
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346794B1

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